


A Stiff Drink

by Smuternatural



Category: Supernatural
Genre: Again, Anal Fingering, Anal Sex, Bartender Dean, Bisexual!Dean Winchester, Blow Jobs, Deep throat, Gay!Castiel, Kissing, M/M, Murder, Rich Castiel, Sex, Shooting, Strangers to Lovers, assume there's a ton of killing, blood/gore, club owner Gabriel, dean is strangely turned on by cas killing people, innocent to killer, just assume there's a ton of butt stuff, mob boss, mobster!Castiel, slight blood play, sugar baby!dean, throat slitting
Language: English
Status: In-Progress
Published: 2019-11-18
Updated: 2020-09-23
Packaged: 2021-02-08 08:02:51
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 25,922
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21472720
Author URL: https://archiveofourown.org/users/Smuternatural/pseuds/Smuternatural
Summary: Dean is a working as a bartender to put his brother through college until his boss gives him an alternative way to make money.
Relationships: Castiel/Dean Winchester
Comments: 91
Kudos: 181





	1. Chapter 1

Dean had a love/hate relationship with his job.

Sure, he got great tips when he wore his skin tight black shirt and jeans that hugged his ass like it was their job. The tips were decent, making just enough to support himself and his brother, Sam, who was in his last year of college. And let's face it, Dean is hot and he knows it. With a wink and a crooked smile he can land anyone he wants for the night.

But that's the thing. Dean was looking for more than a one night stand. Obviously hooking up most nights was great, but lately he just felt like he wanted _more._

More for himself. More for Sam. More money wouldn't be bad either. But for now, working at the The Garrison wasn't all that bad. The regulars knew him by name (and reputation), he was friends with _most_ of his co-workers, and his boss gave him the best hours for making tips. He'd met Gabriel three years ago when he stumbled in the club with Sam, celebrating the fact that he was accepted into Stanford college. Gabriel told him he'd make a killing with those green eyes and freckles and who was Dean to refuse a decent job?

So, that's where Dean finds himself now. Behind the bar slinging beers and vodka tonics to bachelorette parties and college kids.

"Woo-wee, Dean-o! You spend your last paycheck at Baby Gap?"

Dean smirks and keeps his eyes on the beer he's currently pouring. "Jealous, Gabe?"

Gabriel blows a raspberry and pats Dean's back as he passes behind the man. "Please. I could rock a mesh tank top if I wanted to."

"Please, for the love of god," Dean rolls his head back as he flips the handle of the tap up, "spare me the visual." He slides the foaming glass to a pretty woman with long black hair with a wink. She hands him a twenty dollar bill and purrs "Keep the change, handsome."

"Thanks, sweetheart," Dean responds, letting his fingers linger on hers a moment too long before turning to the register.

Gabriel shook his head and tucked his hair behind his ear. "So, Dr. Feel Good, how's that brother of yours? Gettin' all lawyered up?"

Dean smiled wide while stuffing the change in his tip jar. "Hell yeah. He's just about done. Already got a firm lined up that wants him to work for 'em."

"No shit," Gabriel crossed his arms and leaned against the bar. "Must be good."

"He better be. I ain't payin' his tuition for him to fuck off and get wasted every night." Dean grabbed a rag and wiped down the bar, shoving Gabriel out of the way. "Not that he would, though. He's a fucking nerd."

"A six-foot-two tall drink of water nerd," Gabriel sighed, looking off into space. "How the hell're you two related?"

"Would you get the fuck outta here? I'm tryin' to get tips and you're scarin' off all the customers with your weird ass." Dean flicked the wet rag at the other man and ushered him out from behind the bar.

"Oh please," Gabriel snorted, grabbing a bottle of peach Schnapps off the counter before rounding the bar. "You bat those pretty little lashes and you're rolling in it."

"Not lately," Dean mumbled. "I've been thinkin', you should be doin' theme nights. Get some new customers in here."

"I resent that," a voice slurred at the end of the bar.

Dean rolled his eyes and walked over, taking an empty glass off the bar.

"You know we love you Chuck," Dean cooed, refilling the mans glass. "But, couldn't hurt to try it for a week or two."

Gabriel poured himself a shot and swirled the liquid. "Not a bad idea, Winchester." He drank the shot and drummed his fingers on the bar. "Gimmie a list by the end of the week and I'll see what I can put together."

Dean nodded, trying to his his smile as he slid the refreshed beer to Chuck.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Dean tossed his keys in a ceramic bowl as he kicked his door shut behind him. His eyelids were heavy and his feet were sore. Working til three am most mornings took its toll.

He flopped down on his couch as he toed off his shoes. Unbuckling his belt, he pulled it through the loops of his jeans before wriggling and shoving them down to his ankles.

"Fuckin' skinny jeans," he grunted once he was free of them.

He laid his head back on the cushions and sighed, closing his tired eyes. Of course that's when his phone decided to beep at him. He groaned and leaned forward, patting blindly at the denim pile at his feet. Finally retrieving it, he opened the lock screen and read the message.

_From: Douchewad_

_There was a guy in here tonight that asked about you after you left. Said he might have some work for you_

Dean squinted his eyes at the screen.

_From: Dean_

_Not a hooker, Gabe_

_From: Douchewad_

_You sure dress like one, maybe that's what caught his eye ;)_

_From: Dean_

_you gettin to a point anytime soon?_

_From: Douchewad_

_I've seen him around the club once or twice. Good lookin' guy, even better connections. Was asking if you were available_

_From: Dean_

_I don't date customers_

_From: Douchewad_

_I didn't get the impression he's lookin for a date. The dude is loaded, I'm thinkin' it's more of a "You fuck me, I pay for your brothers student loans" kinda deal_

"This can't be real," Dean mumbled to himself.

_From: Dean_

_Ha-ha. Goodnight, Gabriel._

He groaned as he stood up, heading for the bathroom. Bed sounded heavenly right now but Dean needed to scrub the smell of beer and sweat off his skin. He lumbered his way into the bathroom and turned the handle and letting the water warm up. He sat on the toilet lid in his boxers rubbing his eyes when his phone chimed again.

_From: Douchewad_

_I gave him your number._

Dean half groaned, half yelled up to the bathrooms ceiling fan.

_From: Dean_

_Goddamn it Gabe! You can't go around giving out my number!_

_From: Douchewad_

_Why? You give it to every Tom Dick and Henrietta that comes into the club._

Dean was in the middle of typing out a text that would most likely get him fired when his phone chimed again, this time with a number he didn't recognize.

_From: Unknown_

_I apologize in advance, and I realize this is a bit unorthodox, but I got your number from your employer Gabriel. I was interested in talking to you about a job prospect that I think would benefit the both of us. You can reach me at this number anytime, day or night. Goodnight. -Castiel Novak_

Dean stared at his phone as the bathroom filled with steam. This was real. Really real. Gabriel wasn't fucking with him. He mulled it over as reread the text while biting his fingernails.

"Fuck it." He tapped the phone icon at the top of the screen.

Listening to the phone ring was terrifying and exciting at the same time.

The ringing stopped. There was rustling at the other end for a moment. He briefly heard someone or something panting.

"Uh, hello?" Dean tried to keep his voice steady as he jiggled his leg up and down nervously.

The noise stopped and he heard someone clear their throat.

"Hello, Dean."


	2. Chapter 2

**Summary for the Chapter:**

> Dean has an interesting conversation with Castiel and debates his future.

"Is--is this a bad time?" Dean narrowed his eyes, trying to make sense of the noises in the background. He reached over and turned the shower off so he could hear better.

"Not at all," Castiel replied smoothly. "How are you, Dean?"

"M'fine. Uh, I saw your text, obviously. An' Gabriel told me he talked to you at the club."

"Yes, Gabriel and I are---acquaintances." Dean could almost make out a chuckle in the mans voice. Dean heard a soft _thump_ on the other end of the phone. "Would you be willing to meet me sometime? I have something I'd like to talk to you about and I'd rather not hash the details out over the phone."

Dean was quiet for a moment.

"Dean?"

"I'm here, sorry. Uh, yeah, I mean, we can meet and...talk. Just kinda wonderin' what this is all about. Not every day you have a stranger say they have a job for you," Dean huffed.

"I understand, and I promise I'll explain everything when we meet. I'll text you my address."

Dean drummed his fingers on the bathroom sink with his eyebrows pulled together. "Yeah, alright. I don't work tomorrow so I could---"

"Wonderful," Castiel interrupted. "How does noon sound? I'll make you lunch."

Dean smiled. "You sure know the way to a man's heart."

"You have _no_ idea," Castiel all but growled. "See you tomorrow, Dean."

The line went dead and left Dean sitting on the toilet lid in a daze.

Dean woke up to his alarm blaring at him. He patted around blindly until his hand found his phone and shut it off. He sat up, rubbing his face roughly. Picking up his phone, he squinted at the time.

10:45 AM.

"Shit," he groaned, scratching at his belly before standing. He unlocked his phone and checked his messages.

_From: Unknown_

_If you're still able to meet today, my address is 124 North Vine road._

_From: Unknown_

_I hope you like bacon._

A grin spread across Deans face. "Hell yes," whispered.

He showered quickly, cursing himself for not taking one last night. Drying off, he tossed his towel in the hamper and walked into his bedroom naked. Opening his closet, he stood there with his arms crossed and tried to decide what to wear.

He settled on long sleeve dark red Henley shirt and dark blue jeans. He tousled his hair in the mirror until he was satisfied, giving himself a wink. He pulled on a brown leather jacket and his boots before giving himself a once over.

"Not too bad, Winchester," he smirked, grabbing his keys and heading out the door.

The drive to Castiel's was about twenty minutes long and he'd be lying if he said he wasn't nervous. He pulled up to an enormous wrought iron gate with the initials C.N. woven into the center. There was a speaker box to the left with a red button in the center. Dean rolled down his window and pressed it.

"Can I help you," a female voice asked.

"Uh, I'm Dean. Winchester. I'm meeting with Casti---"

Before Dean could finish his sentence, the gate opened with a groan.

"Pull up to the front door please," the voice said.

Dean drove slowly down the gravel driveway, taking in his surroundings. There were artfully sculpted hedges on either side of the lane with red flowers planted at the base. He whistled under his breath when he made it to the house.

Correction- Mansion.

It was a three story house. White pillars stretched up into a balcony on the top floor, which was covered in ivy. A giant fountain was placed directly in the middle of the circular driveway, water spilling out of a pot being held by a naked man.

"Jesus," Dean huffed. He parked his car in front of the main door like he was told and killed the engine.

Climbing out of the car, he flattened his hands on his chest, straightening his clothes nervously. He took the steps that led to the front door two at a time and rang the doorbell. He stuffed his hands in his jacket pockets and shifted from one foot to the other anxiously.

The door clicked open and an older woman in a maids uniform smiled warmly at him. "You must be Dean." She gestured for Dean to come inside and closed the door behind them. "Can I take your coat," she asked warmly.

"Uh, yeah, ok," Dean stammered, shrugging off his jacket while taking a look around. There was a double staircase in front of him, leading off to the left and right side of the house. At the top of the stairs was a life size portrait of an angry looking man he didn't recognize.

"Mr. Novak is in the dining room. This way." She ushered him to the left, down a wide hallway with black and white tiled floors.

Deans heart jumped into his throat as they entered the room.

There was a man sitting at the head of a long dining room table. He wore a crisp white button up shirt with the sleeves shoved up to his elbows. A cigarette hung loosely off his lips as the smoke curled up into the air. His hair was shiny black and slicked back, save for one lock that curled down over his forehead. The held a newspaper in front of him, silently reading yesterdays news.

The maid cleared her throat which made him look up from his paper. His piercing blue eyes locked onto Dean, staring for a moment before folding the paper and setting it on the table. He rose from his seat slowly as Dean tried to remember how to breathe.

"Dean. Welcome to my home," he said while shoving his hands in his pockets

And holy shit if Dean wasn't already half hard he was now. The deep gravel of the mans voice settled in his chest like an anchor and threatened to pull him under.

"Uh---hi," Dean managed to say.

The man walked over and nodded to the maid. "Thank you, Naomi, you can leave us now."

She lowered her head and smiled before turning to leave the room.

"It's nice to meet you face to face. I'm Castiel if you haven't already guessed," he said, reaching out a hand.

Dean pulled his hand out of his pocket and clasped Castiels' hand firmly. They were big, calloused, and Dean couldn't stop imagining them wrapped around certain parts of his body.

"Yeah, I got that," Dean huffed, pulling himself from his thoughts. He realized he was still shaking Castiels' hand and tore it away, slipping it back into his pocket.

Castiel grinned and motioned towards the table. "Please, have a seat. Lunch will be ready soon and I thought we could talk while we wait."

He returned to his seat at the head of the table and Dean followed behind, sitting in the chair next to him. He fiddled with his shirt nervously as he watched Castiel shove his sleeves higher up.

"I'm assuming you have questions," Castiel cocked an eyebrow as he lit up a cigarette.

"About a hundred," Dean murmured.

Castiel huffed through his nose and ashed his cigarette. He sat back and crossed his arms.

"I work for a very---demanding company. It doesn't leave a lot of time for personal relationships," he began. He took a long drag of his cigarette and blew it towards the ceiling. "I've noticed something missing in my life lately and wish to remedy that." He eyed Dean and smirked. "I know you work at The Garrison but even with how incredibly good looking you are, I'm assuming you don't make enough to support you and your brother."

Dean's eyebrows shot up. "How did---"

Castiel waved a dismissive hand in the air. "Gabriel has a big mouth," he explained. He put his cigarette in the ash tray and turned to fully face Dean.

"I'm going to be blunt, Dean. I have a lot of money and I need to keep up appearances when I go to business functions. I'm tired of my family and...coworkers trying to set me up with random people I have no interest in. I would pay you, handsomely of course, to be my romantic partner. In return, you could pay for your brothers tuition and housing, plus whatever else you desire."

Dean opened his mouth and closed it a few times before taking a deep breath. He sat back in his chair and let it out.

"So I'd be your sugar baby," Dean raised an eyebrow at the man next to him.

"Essentially, yes. But I hate that term," Castiel waved a hand in the air. "Think of it as a business agreement. You help me---"

"I help you," Dean finished.

"Exactly," Castiel answered with a wicked smile.

Dean sat forward and rested his elbows on the table with his fingers laced together. 

"How much we talkin' here? Sam's books alone are $3,000 a semester and his housing---"

"$10,000 a month," Castiel stated.

Dean's eyes widened comically before he laughed out loud. "Seriously, come on man."

Castiel didn't blink.

"You're serious. $10,000 a month to, what? Be your arm candy at fancy events? Make you look good for the boss and---"

"And sleep with me," Castiel said bluntly. "Whenever I desire."

It was Dean's turn to not blink. His heart was hammering in his chest and he felt like he was going to pass out or throw up.

Just then, the dining room doors swung open. A women in uniform pushed in a cart with silver trays and a bucket with beer in it inside the room. She rolled it up to Castiel and bowed her head with a smile before leaving the room.

"I hope you're hungry," Castiel said, uncovering the trays.

Underneath were giant, gourmet-looking burgers, complete with an enormous amount of bacon.

Dean mouth watered for multiple reasons as he looked at the man next to him

"Starving," he whispered.

They finished their lunch in relative silence. Dean was pretty hungry and the burgers were phenomenal. He wiped his mouth off with probably the most expensive looking napkin he's ever seen and tossed it on his plate. He glanced over to see that Castiel was staring at him.

"Do---do I have something on my face?" Dean wiped at the corner of his mouth with his fingers.

"No. You're just--," Castiel licked his lips and let his teeth scrape over his lower lip. "Never mind." He cleared his throat and fidgeted with his sleeves. "I assume you'd like to think over my proposition?"

Dean nodded, staring at the mans spit slicked lip.

"Take the rest of the week and get back to me. Naomi?"

A second later, the door popped open and Naomi smiled at Dean, handing him his jacket.

Dean stood and nodded his head, silently thanking the maid. He shrugged on his jacket as Castiel stood, holding out his hand.

"I hope to hear from you very soon," Castiel said in the same deep voice as before.

"Yeah--uh, yeah," Dean stuck his hand out and shook the other mans tightly. "I'll--I'll call you."

"I'll be waiting," Castiel smirked.

Dean drove home in silence trying to make sense of what just happened. He pulled into his garage and shut the car off. Sitting there he tried to calculate how much it would actually cost him to pay for Sam's needs and his own. He looked at his modest apartment, wondering what it would be like to be able to afford something bigger and newer. He patted the steering wheel and smiled.

"Don't worry, Baby. No matter what happens I'd never get rid 'a you."

_What's the worst that could happen _he thought to himself.

He pulled out his phone and opened his texts, scrolling to his and Castiels' last conversation. He quickly added the mans name to his contacts and typed out a message.

_From: Dean_

_I'm in._

His heart pounded in his ears as he waited for a response. Luckily he didn't have to wait long.

_From: Castiel_

_Excellent._

_From: Castiel_

_I can't wait to get started._


	3. Chapter 3

**Summary for the Chapter:**

> Castiel has a meeting with his boss.  
Dean talks with Gabriel.

Castiel's shoes clicked softly across the marble floor. He nodded to the receptionist behind a large desk who was typing behind a computer screen. She smiled warmly at him and said "He can see you right away, Mister Novak."

"Thank you Bella," he smiled before walking up to the large doors. He shoved them open and walked inside, letting the doors close quietly behind him.

"Castiel! It's good to see you." A balding man stood and rounded his desk, holding out his hand.

Castiel pressed his lips together and nodded. "Zachariah, it's been a while." He shook the mans hand briefly before sticking his hands in his pants pocket.

"Too long," Zachariah smiled, showing his yellow teeth. "Come in! Sit, sit." He gestured towards a leather chair in front of his desk as he made his way back to his. He sat down with a grunt and slid a folder towards Castiel.

"I have a job for you," Zachariah said quietly, raising his eyebrows slightly.

Castiel took the folder off the desk and opened it, leafing through the papers. Multiple pictures showed a man walking down the street and going into various shops. Further in the stack was a frame by frame shot of the same man, naked inside an apartment building, standing above a woman in a blindfold.

He closed the folder and sighed. "Who's he sleeping with?"

Zachariah puckered his face. "Mm, I'm not at liberty to divulge that information. Let's just say," he sat back in his chair and rocked lightly, steepling his fingers, "someone is willing to pay our company handsomely to make it stop."

Castiel pulled out a pack of cigarettes and held them out to Zachariah who declined with a wave of his hand. He lit one up and took a deep drag. "What's the time frame," he asked, blowing the smoke out of his nose.

"As soon as possible. The client has previously hired two other contractors but," Zachariah shrugged.

"Consider it done." He ashed his cigarette in the crystal dish in front of him. "Anything else?"

A wicked smile spread over Zachariah's face. "Actually, I have a friend who is interested in meeting you---"

"No thank you," Castiel huffed, taking another long drag.

"Castiel," the bald man slumped, "why won't you let anyone help you find a suitable partner? You must be lonely. We have all sorts at our disposal. You seem so---," Zachariah wiggled his fingers towards the other man, "pent up."

"If you must know," Castiel stood and snuffed out his cigarette, "I've recently met someone. Thank you for your unwanted interest in my personal life, but it isn't necessary."

Zachariah clapped his hands together as his eyes widened. "Wonderful, Castiel! Truly! You have to bring him to the boss' anniversary this weekend. I can assume he doesn't know exactly what line of business you're in?"

He shook his head and sighed, grabbing the folder and waved it in the air. "I'll call you when it's finished."

Dean spent the rest of the night sitting on his couch, staring blankly at the TV. He thought about texting Sam and letting him know about his new business venture, obviously omitting the part where he's basically selling his ass for his brothers college degree. Thinking better of it, he pulled out his phone to text someone else.

_From: Dean_

_How do you know Castiel?_

_From: Douchewad_

_It's your night off. Why are you texting me and not getting laid?_

_From: Dean_

_I'm serious. The guy is fucking loaded and said you guys are 'acquaintances'. How the hells that happen?_

_From: Douchewad_

_Let's just say I had a little problem and he solved it for me_

_From: Dean_

_I swear if you did for him what he wants me to do, the deal is OFF_

_From: Douchewad_

_Don't worry your artfully styled head about that. Trust me, Cas is a good guy and bends over backwards for the people he cares about. You're in good hands. Real good ;)_

Dean sighed and tossed his phone on the couch. He couldn't get his mind off Castiel and his stupidly gorgeous face. He did say that he could talk to him any time if he had questions, so Dean picked his phone back up.

_From: Dean_

_Sorry if you're busy. I just had a few things to ask you, since were gonna be in 'business' together_

He waited a few minutes for a response. Ten minutes went by agonizingly slow before his phone chimed.

_From: Castiel_

_Ask anything you'd like_

_From: Dean_

_I don't know man, I'm new to all this. I'm just a bartender, not used to bein asked to sleep with someone for a fuck ton of money. Which I guess is my first question- Why me?_

Dean was shaking his leg nervously, thoughts running through his head. He stood up quickly and walked over to the fridge, pulling out a beer and popping the top. He chugged half of it before his phone went off again.

_From: Castiel_

_You mustn't think of yourself like that. You aren't just sleeping with me. You're helping me fill a void in my life. We will act like any other couple in public, go to company functions, have dinner together. Normal couple things. I just compensate you to be mine._

Dean grimaced at the word "compensate".

_From: Dean_

_I guess I'm just having a hard time with the money part._

_From: Castiel_

_If the amount I have set isn't enough I can offer more._

_From: Dean_

_No, man, it's definitely not that. I guess I just have to experience it to see what it all entails. Do you have anything you'll need me for soon?_

_From: Castiel_

_Actually, yes. There is a party I'd like you to attend with me this Friday. I've already cleared your schedule with Gabriel so you're free._

Dean rubbed a hand down his face as he stared at his phone. "Jesus Christ," he muttered.

_From: Dean_

_Alright, I can do that. How fancy we talkin here, Cas? Do I need to go shopping?_

_From: Castiel_

_I'll pick you up Friday at 5 pm and take you shopping._

_From: Dean_

_I can dress myself, man. Just tell me the dress code_

_From: Castiel_

_And prevent me from watching you try on suits? I think not._

Deans throat went dry.

_From: Dean_

_Yeah, ok. We can do that. See you then_

_From: Castiel_

_Goodnight, Dean_

_From: Castiel_

_Also, if it's not too muck to ask, don't touch yourself until we see each other again. I'd like to be the next person to put my hands on you._

Dean died. He died and floated above his body. He could see himself, eyes wide reading that last text.

When he got his thoughts back into some semblance of order, he texted back

_From: Dean_

_Yes, sir_

Castiel smiled as he pocketed his phone.

"Apologies. Personal issues needed tending to," he muttered. He looked down at the man he was currently pinning to the floor with his foot. The man gasped and choked on his own blood.

"Please," the man whispered hoarsely. "I'm sorry. I'll never see her again, I swear," he sputtered, gripping Castiel's ankle tightly.

Castiel cocked an eyebrow and huffed a laugh. "Little late for that isn't it?" He pressed his heel down hard, feeling it pop and crunch under his foot and he watched the light leave the mans eyes.

He pulled out his phone and hit a button.

"It's done."


	4. Chapter 4

**Summary for the Chapter:**

> Dean tries to distract himself with work and Castiel makes it very hard for him to focus.  
Castiel takes Dean to get fitted for a suit.  
Dean gets ready for the party.

"Here ya go, Chuck."

Dean slid the frothy glass towards the already drunk man. He took a few dollars off the counter that were already laid in front of the man and stuffed them in the register.

"Hey, Dean-machine," Gabriel rounded the bar giving his employer finger guns. "How goes it? Or should I say, how's Cassie?" He winked at Dean and pulled a lollipop out of his pocket. He ripped the wrapper off and tossed it towards the garbage can, totally missing.

"Goddamn it, Gabe," Dean sighed. "I'm the one that's gotta clean up behind here. Can you at least try to make it in the basket?" He walked over and picked the wrapper up and tossed it in the garbage.

"Yeesh, what's up your ass," Gabriel mumbled around his candy.

Dean shot him a glare and turned his attention to a customer at the bar. "What can I ge--" The words got caught in his throat when he looked at the man in front of him.

"Hello, Dean," Castiel purred. He drummed his fingers on the bar and smiled. "Can I get a drink?"

"Yeah, Dean-o, make it a stiff one," Gabriel said with a wink.

Dean flushed instantly, his cheeks and ears turning red. "What can I get ya, Cas?"

Castiel ran his thumb over his bottom lip and contemplated. "Whiskey neat, please."

His voice rumbled through Dean's chest, making his hands shake lightly.

"Yeah, ok." Dean turned around to the shelf and grabbed the most expensive bottle. He looked up into the mirrors behind the shelf to see Castiel's eyes raking over his body.

"So Cassie, how's tricks," Gabriel asked with a knowing smirk.

"Gabriel, how many times have I asked you _not _to call me that?" 

Dean pressed his lips together, pouring Castiel a generous amount of whiskey. He handed it to him instead of sliding it across the bar, their fingers grazing gently.

"Thank you, Dean. And as for tricks, Gabriel, things are looking up." He smirked at Dean and took a sip of his drink.

Dean blushed even harder.

"Good," Gabriel slapped the bar. "Alright, well I'm gonna go take care of some business in the office." He tapped the bar once more before saluting and heading back to his office.

Castiel swirled the brown liquid before taking another drink. "So, Dean, how are you?"

Dean wiped his sweaty palms on his jeans before leaning on the bar.

"Can't complain," he replied shakily.

Castiel squinted over his glass. "I make you nervous," he stated.

Dean looked down and huffed. "Is it that obvious?" He looked up through his lashes, watching Castiel's eyes widen slightly.

"It is." Castiel dipped his head and crooked a finger, beckoning Dean closer.

Dean leaned over the bar slightly, almost tasting the whiskey on the other mans breath.

He reached between them and ran his fingertip over Dean's cheek. "Your cheeks flush every time I'm near you from here to here." He dragged his finger up to Deans ear. "Your breath catches in your throat when I catch you off guard and you get an adorable little stutter when I ask you a question that makes you nervous." He ran his thumb down Dean's lower lip, dragging it down roughly.

"Jesus Christ, Cas," Dean sighed. He let his head drop to his chest as he let out long breath. "You talk to everyone like that?"

Castiel lifted the other mans chin so they were eye level. "No, never actually." He slid his finger off the tip of Deans chin and reached for his glass, never breaking eye contact. "I have a vested interest in you, Dean. You make me---," he shook his head with a grin before swallowing the rest of his drink. He cleared his throat and stood up, pulling out his wallet.

"Hey, no way. It's on the house," Dean held up a hand and shook his head.

Castiel huffed a laugh. "I'm not paying for the drink." He pulled out a folded piece of paper and slid it across the bar. "I'm paying you."

He watched in shock as Castiel hooked his jacket over his shoulder and walked out of the bar. After coming back to reality, he unfolded the piece of paper in his hand.

"Fuck," he whispered. It was a check for $10,000.

"Need 'nother one over here," Chuck slurred, pulling Deans attention from the check.

He quickly filled the mans glass and sloshed it over to him, spilling some down the side. He turned on his heel and bolted to the office.

"Hey!" Chuck yelled, grumbling something about alcohol abuse.

"Gabe," Dean knocked on the door before opening it. "Gotta talk to you about---Jesus fuck, Gabe! Lock the fucking door next time!" He closed the door enough that he couldn't see what was going on in the office, but open enough that he could hear his boss clearly.

Gabriel poked his head up over the shoulder of a blonde haired man. "Or you could wait for me to respond! What the hell do you want, Winchester?"

Dean bit his lip before responding, sucking in a deep breath through his teeth.

"I quit." He closed his eyes and braced for Gabriel's wrath.

"Don't be a stranger," he called out.

"Wait, what?" He opened the door and poked his head inside, instantly regretting it.

Gabriel's head was in the blonde guys lap. He popped off and licked his lips. "I figured once I hooked you and Cassie up that'd be curtains for you. That's why I hired Max. Oh, my bad. Dean, Max. Max, Dean."

Max hooked his chin over his shoulder and smiled, batting his lashes. "Thanks for the job," he winked before gripping Gabriel's hair and shoving his head back down.

"Jesus fucking Christ," Dean groaned. "See ya 'round, Gabe."

Gabriel's response was muffled.

Dean shook his head and closed the door. He rounded the bar one last time to grab his jacket. Waving goodbye to Chuck, he gave the place a once over before pushing the door open and stepping out onto the sidewalk. 

It was kind of sad, really. He'd worked there for three years, he made friends, hell he might have even considered some of them family. He took a deep breath and turned around, heading for his car when he heard a familiar voice.

"Need a ride?"

Dean stopped in his tracks and smiled. He turned to see Castiel leaning against a sleek black town car, suit jacket still hooked over his shoulder.

"Nope. Do you?" Dean smiled and gestured towards his car with a nod.

Castiel narrowed his eyes and smirked before ducking his head into the car and saying something to the driver. He shut the door and the vehicle pulled out and drove down the road.

"Where are we going," he asked, walking up into Dean's personal space.

"Well, seeing as I just quit my job, I'd say just about anywhere you wanna go."

Castiel raised an eyebrow. "Is that so?"

Dean nodded and fiddled with his jacket.

"Why put it off until Friday? Let's go get you a new suit. Or three."

Dean drove where Castiel instructed, hyper aware that they were no longer in the side of town Dean was accustomed to. High rise buildings occupied the side of the streets, ornate looking shops with tall glass windows showed off their very expensive items.

"It's just ahead," Castiel informed Dean. He parked in front of the building, noticing the same sleek car on the other side of the street.

"They follow you everywhere?" Dean asked as he climbed out of the car.

Castiel squinted over at the vehicle and smirked. "Perceptive, aren't we?"

Dean huffed and shut his door before rounding the hood of his car. "Tell whoever you're workin' for they need to learn to blend in. That kinda car sticks out like a sore thumb to guys like me." He looked Castiel in the eye and raised an eyebrow. "Government?"

Castiel scoffed and rolled his eyes. "Please," was all he said. He opened the shop door and let Dean go in first.

"I am so out of my element," Dean whispered to himself.

The shop was gigantic, much bigger on the inside. A crystal chandelier hung from the ceiling, casing sparkling lights over the walls. Racks of suits lined the walls, large white seats were scattered throughout the store with chilled champagne in an ice bucket next to each one.

Dean snapped his mouth shut as Castiel gently took his elbow and motioned him forward.

"Castiel! What a treat," a man called from behind the marble counter. "Dear, it's been too long."

The man walked over and kissed Castiel lightly on the cheek (which shouldn't have made Dean bristle, but it definitely did) before turning his attention to Dean.

"Oh, my. What do we have here," the man purred.

"Balthazar, this is Dean. Dean, meet my tailor Balthazar," Castiel gestured between the two.

Dean stuck out his hand and and shook the other mans. "Good to meet you."

Balthazar looked Dean up and down while still holding Deans hand. "My God, Cassie, he's marvelous. Where on Earth did you find him?"

"At a bar," Dean said squaring his shoulders.

Castiel laughed outright at that. Dean had never heard him laugh before and it was wondrous, like music to his ears.

Balthazar raised an eyebrow but said nothing to his comment. "Alright then, the usual my dear?"

Castiel nodded and ushered Dean to the middle of the shop towards a platform. He held out his hand for Dean to take while he was stepping up onto it, their palms sliding against each others.

"Jacket," he said simply, holding out his hand.

Dean shrugged it off and handed it to the other man.

"Oh. Thanks, Cas," Dean mumbled, offering a small smile.

"So, Dean," Balthazar pulled a measuring tape out of his waistcoat, "have you ever been fitted for a suit before?"

"Uh, no. Only ever rented one," he admitted.

"Such a disgrace. A man like you should be drenched in the finest silk and buttoned up in a form fitting jacket," he winked.

Sitting down on one of the leather couches, Castiel crossed his ankle over his knee, draping his arm over the back of the couch. "And that's exactly why we're here," he said darkly, eyeing Dean once he was settled on the platform.

"This is going to be so much fun," Balthazar clasped his hands together with a grin.

Thirty minutes, and one awkward inseam measurement later, Dean joined Castiel on the couch. Castiel handed Dean a glass of champagne and rested his hand on the mans lower back.

"That wasn't so bad now was it," Castiel bit back a smile.

"That dude is _all _hands," Dean huffed into his glass before downing it.

"It's his job, Dean. Yes, Bal can get...a little carried away, but he's nothing if not professional." His blue eyes sparkled as he took Deans glass and refilled it.

"Guess so. S'just weird, y'know? I'm not used to all this," he gestured towards the store.

"You'll grow quite accustomed to the lifestyle I'm sure. Although, it does take some acclimating to."

Dean turned to fully face Castiel. "Do you hear yourself when you talk," he laughed.

Castiel reached over and ran a finger down Dean's jawline. "I love hearing you laugh," he said, watching Dean's eyes widen at the touch.

Swallowing hard, Dean ducked his head. "I, uh, I was thinkin' the same thing earlier. Never heard you laugh before. S'nice."

"Dean, we've known each other for less than a week. There are many thing you'll learn to like." Castiel turned Dean's with his finger, bringing their lips close enough that they could easily kiss.

"Cas," Dean whispered, his eyes lowering to the other mans mouth.

"All set, Cassie." Balthazar came into the room with three suits draped over his arm. "Oh my, am I interrupting?" He put a hand on his hip and popped it out, raising an eyebrow.

Castiel released Dean and stood, leaving the other man in a haze.

"Thank you, Bal. I'm sure they're beautiful as always." He took the suits and leaned in, letting the tailor kiss him on each cheek. "Coming, Dean?"

Dean snapped his eyes to Castiel and stood instantly. "Yeah-yes. I'm ready."

Castiel handed Dean the suits carefully. "Take these to the car. I'll be out in a moment." He reached into his back pocket and pulled out his wallet.

"Hey, no. I got this," Dean whispered, pushing Cas' wallet away.

Castiel pressed his lips together and tilted his head, reaching up to cradle Dean's cheek. "Oh, my sweet boy," he smiled. "Go to the car."

Not one to press his luck, Dean nodded and shot a wave to Balthazar.

"See you soon, I hope. It was wonderful to meet you Dean."

The door of the Impala clicked shut and Dean turned around to hang the suits from a hook in the backseat. He started the engine and drummed his fingers on the steering wheel impatiently. Glancing out his window, he noticed the sleek black car was missing, but in it's spot was a grey van with a florists logo on the side. He tipped his head back and barked a laugh. He was wiping a tear away from his eye as Castiel climbed into the passenger seat.

"Something funny?" He quirked an eyebrow at Dean.

"Nah, Cas. Not a thing," he smiled.

Friday came faster than Dean had anticipated. He had spent the week with Castiel going to lunches and getting to know each other. He learned that Cas had two brothers and a sister who were all adopted. He still wasn't exactly sure what type of business he was involved in, but he didn't really mind. Castiel treated him well and Gabriel was right, he would bend over backwards to help out people he cared about. Wednesday evening Dean stupidly ran out of gas on the side of the road in a not-so-great neighborhood. Castiel was there in ten minutes with a gas container and a crooked smile. Dean didn't dare comment on the strange bulge in the back of his dress slacks and the tired look in his eyes. All in all, he was enjoying himself.

Except for the fact that Castiel already paid Dean and they haven't so much as kissed yet, but not for lack of wanting.

He pushed those thoughts aside as he tried to straighten his collar. The new suit fit him comfortably like an extra set of skin, draping and hugging where it needed to. Castiel was right, Balthazar was amazing at his job. The dark navy blue fabric felt soft against his fingertips as he smoothed it down over his body, deciding to pop the top button and fan it out over his chest. He was raking his fingers through his hair in the mirror when he heard a knock at his door.

His new shiny shoes (thanks again, Cas) carried him to the front door and pulled it open.

He whistled under his breath and looked Castiel up and down.

"Damn, Cas. Lookin' good." He licked his lips and watched the other mans eyes light up.

"Thank you Dean. You're looking rather...enticing yourself," he said with a low growl. "I may have to keep an eye on you tonight." He reached over the thresh hold and ran his fingers down Dean's jawline.

Dean scoffed and ducked his head. "What, the creepy florist van won't be there to watch every move I make tonight?"

Castiel pulled his hand away like he was burned. "What?"

"M'just jokin', Cas. I don't care if you have your own private security watchin---"

"No," Castiel held up a hand and pushed Dean's into his apartment, kicking the door shut behind him. "What van?" His eyes flared as he waited for Dean's answer.

Dean raised an eyebrow high and huffed. "Uh, the grey one outside the tailors the day you bought me this," he gestured towards the suit. "By the way man, you gotta let me pay at least a little---"

"Stop talking," Castiel said sharply. He pulled out his phone and walked over to Deans window and opened the blinds a crack. He smashed a button and held the phone up to his ear.

"It's me....yes we're ok. I think," his eyes flicked to Dean and back out the window, "I think we're being followed....no, not one of ours....Dean," he turned to the other man who was standing there in shock. He walked up and calmly took Deans hand and gently squeezed it. "Did you happen to get a look at the license plate?"

Dean closed his eyes and tried to think. "Uh, I dunno. It was a grey van, florist logo on the side." He shook his head, thinking hard. "LB...47, something. I'm sorry Ca--"

Castiel leaned in and kissed Dean on the cheek gently. "Did you get that?....Good. Keep me updated." He clicked his phone off and turned to Dean. "Ready to go?"


	5. Chapter 5

**Summary for the Chapter:**

> Dean goes to a party with Castiel  
Cas is forced to tell Dean what he does for a living  
Michelle is Michael's female vessel  
**Warning- There will be smut in this chapter**

"Dean," Castiel held out his hand, "are you ready?"

He stood there with his mouth open and eyes bulging, doing his best impression of a dead fish. "N-no. No, I'm not ready, Cas. The hell was that all about?"

The other man sighed and looked at his watch. "We really have to be going," was all he said before grabbing Deans hand and pulling him along behind him. He dragged Dean out the door and into a dark blue car that almost matched his suit. He sat down with a huff, straightening his suit jacket then nodded to to driver. He pressed a button on the door of the car and a black divider climbed it's way up to the roof of the car, leaving the men in the backseat their privacy.

Castiel rested his hand on Dean's thigh gently once the car started moving. "I understand that you have questions, but I'm not cleared to tell you anything yet. I'm hoping that will change after tonight."

Dean blinked rapidly. "So you do work for the government," he guessed.

Castiel smiled warmly and reached up to hold Dean's chin. "You're so---good," he whispered in awe. He pulled Dean closer by his jaw, licking his lips and staring at the younger mans mouth. "I look forward to eradicating that one day."

Barely holding back a moan, Dean brushed his nose against Cas' softly. "Why wait," he said, surprising himself. In an act of sheer bravery Dean let his mouth fall open, his tongue dancing behind his teeth, and sucked Castiel's lower lip into his mouth. He rolled it with his tongue once before biting down.

Castiel groaned loudly, gripping Dean roughly on either side of his neck and digging his fingers into the tender skin there. He pulled Dean off his lips and bit down the mans jaw, sucking little red marks along the way. Dean gripped Cas' jacket tight, panting and moaning as the other man assaulted his neck.

"Fuck, Cas," he breathed, ducking his head and capturing Cas' lips again. His hand found it's way between the older mans thighs and cupped him there, relishing in the fact that he was making Cas lose control.

"Dean," Castiel warned in growl, rutting once into the mans hand. He pulled back with a strained grunt and gently removed Dean's hand from his lap. His eyes were wild and almost black as he licked his spit slicked lips. "As much as I'd like to---," he shook his head, trying to regain any semblance of brain function.

"Right," Dean nodded with a frown. "No, I get it." He looked down at his wringing hands and sighed.

Castiel's eyes widened. He reached over to stop Dean from pulling off his own fingers. "Dean, I want to. More than you probably realize." His tone was so sincere and desperate that it made Dean smile. "I just don't think showing up to to my boss' party covered in hickeys and come would make a good impression."

Dean laughed outright and pinched his eyes shut, imagining what that might look like. "Ok, yeah I understand Cas. Party now, this---," he gestured between them, "later?"

Lowering his gaze to Deans mouth, Castiel licked his lips again. "Later."

A very sexually frustrating drive later, they pulled up to an even more extravagant mansion than the one Castiel lived in. It was a massive and white with giant marble pillars similar to Castiel's but much older. They pulled up to the valet and were given a ticket as they stepped out of the car.

Dean watched as women dressed in silk gowns, their necks dripping with diamonds, glided past and into the house. A pressure on his elbow made him turn to see Castiel smiling.

"Ready?"

"As I'll ever be I guess," Dean mumbled.

"Don't be nervous," Castiel soothed while running his fingers through Dean's mussed hair, "you don't have to speak to anyone if you don't want to. I'll be with you the whole time." He leaned in close to Deans ear as they walked up the stairs into the house. "Just remember what comes after we're through here."

Dean bit his lip as he straightened his posture and nodded shyly.

They walked into a wide open area where very rich looking people were talking and sipping very expensive champagne. Dean tilted his head to Cas', taking stock of about a million dollars worth of art on the walls. One piece being the very same piece that hung in Castiel's home.

"Who exactly is this party for again?"

Castiel thanked a waiter after taking two flutes of champagne off his silver tray. "My boss." He handed Dean a glass and clinked his against it in a small 'cheers'. "Technically," he said after swallowing, "my boss' boss' boss."

"The head honcho," Dean raised his eyebrows. "Better be on my best behavior then," he smirked, eyeing Castiel over his glass.

Castiel wrapped his arm around Dean's waist, pulling him flush to his hips. "God, I hope not," he smiled before lightly kissing Dean on the cheek. He watched as blush crept up the younger man's cheeks and peaked at his ears.

Dean ducked his head and pressed his lips together. "Plenty of rooms in here. We could---"

"Castiel!" a voice yelled from across the room.

Cas immediately let his head drop to Dean's shoulder and groaned. "Kill me now," he mumbled into the mans neck. He picked his head up and plastered on fake smile. "Zachariah. Hello," he said stiffly.

"Loosen up, Cas. It's a party," the bald man raised his glass and clinked it against Cas'. "And this must be---," he man raised an eyebrow, holding out his hand.

"Dean Winchester. Good to meet you." He reached out and shook the other mans hand.

"Winchester," Zachariah tapped his lips with a finger, "why does that sound familiar?"

Castiel bristled. "Where is the guest of honor?" He looked around the crowd, obviously trying to change the subject.

Zachariah rolled his eyes. "Upstairs. Actually, that's why I came over. She'd like a word with you." He glanced at Dean briefly. "Alone."

Once Dean convinced Castiel that he would be fine by himself, he kissed him on the cheek and followed Zachariah up the grand staircase. They walked side by side down a long hallway lined with portraits of old men. Once they reached the end of the hall, Zachariah knocked on the large mahogany door.

"Come," a voice said.

He pushed the door open and held his hand out for Castiel to enter. Once Castiel was inside, Zachariah closed the doors behind them, leaving the two alone.

"Castiel," the woman purred. She stood from her leather chair and rounded the desk she was sitting at. Her skin was a gorgeous shade of mocha with eyes to match. Her short black hair was artfully pinned to her head with diamond barrettes.

"Michelle," Castiel reached out a hand, "good to see you again. It's been too long."

Michelle raised an eyebrow and scoffed at Castiels' gesture. She batted his hand away and leaned in to kiss him on each cheek slowly. "I'm told you came with a date tonight," she accused. She slipped her hand between Cas' waist and arm, reaching behind him. She pulled back a small silver bag and took out a pack of cigarettes.

"I did. His name is Dean." Castiel watched as Michelle searched for something in her purse.

"Damn it," she whispered, tossing the bag on a nearby chair. "Do you have a light?" she asked, putting the stick between her lips.

Digging in his pockets, Castiel pulled out a lighter and lit it for her. "Do you mind?" he asked, patting his thigh.

"By all means," she said, turning her back to the man and walking back to her chair.

Castiel lit up a cigarette and joined her, sitting in front of the desk. "You wanted to see me?" he asked, taking a drag.

"I did," she smiled, ashing her cigarette. "I have a job for you."

Castiel raised his eyebrows. "Mich, it's your party. Must we do business now?" he asked, blowing smoke out through his nose.

She chuckled and sat back in her chair, elbow propped up on the arm of her chair holding her cigarette lightly. "Yes, we must. The job needs to be done now. Tonight."

Rolling his eyes, Castiel sighed and leaned forward. "Dean doesn't know what I do for a living and I'd like to keep it that way for as long as possible. Also," he pointed a finger at her that was holding his cigarette, "we know how this turned out last time you asked me to remove a guest from one of your parties."

Michelle smirked. "Oh please, he was a rat and you know it. Besides, nothing like a little public execution to show the family their place."

Castiel pursed his lips and narrowed his eyes. "I suppose you're right. Who is it?"

Dean was sitting alone at the bar, champagne long forgotten for a beer. He sat there picking at the label when he felt something brush his shoulder. He smiled lightly and turned around.

"'Bout time," he said turning his head. "Oh. Sorry, I thought---"

A woman stood next to him smiling. "Thought what, handsome?" She flipped her long black hair over her shoulder revealing an incredibly low cut dress.

Dean snapped his eyes forward, pointedly avoiding her chest. "Thought you were someone else is all," he muttered.

She hummed under her breath as she slid onto the seat next to him. She leaned in close to Dean. "I could be someone else, if that's what you're into." She scraped her nail gently down his cheek.

Dean pulled away and scowled. "Sorry lady, I don't pay." He picked up his beer and was about to leave when the woman grabbed his arm.

"I'm just playing with you, sweetheart. Couldn't resist. Castiel never brings anyone to these ridiculous parties so I thought I'd have some fun." She held up two fingers to the bartender, signaling that she'll have a beer and to refresh Dean's.

"You could at least speak to the guy," Dean grunted, thinking back on all the times that customers assumed he knew what they wanted with a wiggle of a finger.

The woman smiled and held out her hand. "Ruby," she purred.

Dean shook her hand quickly before pulling his hand away. "Dean," he offered.

Her eyes sparkled as she looked him up and down. "Dean," she hummed, "hope to see you around more often." She left her beer on the bar as she slid off the seat and sauntered away.

_The fuck was that about _Dean thought to himself.

Bless Castiel for his perfect timing, because moments later he felt an arm around his waist and a scruffy cheek graze against his own.

"I really hope that's you and not another person comin' to hit on me," he chucked as he turned around.

Castiel raised an eyebrow. "You've been getting hit on?"

Dean rolled his eyes. "Don't worry, I think I scared her off. How was your meeting?"

Castiel held out his hand to Dean who let himself be led onto the dance floor, which honestly was just a large room with all the furniture pushed against the walls.

Castiel took Dean's hand properly and held it high, clasping it in his own before snaking his arm around the younger mans waist. He let Castiel lead, and to his surprise, he only stepped on his foot twice before getting the rhythm down. They smiled at each other as they made their way around the floor, very aware that everyone was watching them. Dean didn't seem to care, let 'em watch.

The song was interrupted by loud applause. Much to Dean's dismay, Castiel let go of his hand and turned to the staircase. He joined in the applause as everyone watched Michelle descend the stairs slowly. She nodded to random people with a smile on her face. A waiter handed her a champagne flute before she turned to address the crowd.

"Thank you all for being here tonight. I know schedules rarely line up, so I'm truly grateful for those of you who were able to attend. As you know, this is the seventh year I've been head of the company. I cannot be more pleased with the work we're doing here."

She glanced to Castiel, then her eyes landed on Dean with a smile.

"Also, to all the new faces here tonight, I'd like to talk to each of you before the night is over, so please find me when you have a moment. For now," she raised her glass high, "drink and have a wonderful time."

The room erupted in applause again as she took a sip of her drink and waved to them all.

"That's your boss?" Dean asked before taking a sip of his beer.

"What, you were expecting an old wrinkly man?" Castiel nudged Dean with his elbow.

"Well---yeah. Kinda. I mean, I kinda assumed it was him," he gestured with his beer to the giant painting at the top of the stairs.

Cas glanced at the picture, then to a group of people standing next to it which happened to include Ruby. He shook his head and cleared his throat. "He hasn't been around for a long time. He was the best boss I've ever had though. He built all this," he gestured towards the people.

"You knew him well then," Dean guessed.

Castiel lips tightened into a small smile. "Would you join me outside? I could use a smoke."

  
They stepped out into a lush garden at the back of the house. Castiel lit up his cigarette and took a long drag, blowing it up into the night sky.

"Are you ok? You seem---stressed," Dean crowded into Cas' space and let his fingers trace random patterns into his shirt. 

"A little," he admitted. "Getting better now though." He licked his lips as his eyes bounced from Dean's eyes to his mouth. "I want to kiss you, but I'm not sure how you feel about smoking." He licked his lip instinctively and looked down at his cigarette.

Dean huffed and pulled away from Cas, taking the cigarette from between the mans fingers. He lifted it to his lips and took and drag then blew it out his nose.

"There, now we both taste like it," he whispered.

Castiel grabbed Dean by the collar and spun him around, walking him backwards until Dean hit the side of the house. He wasted no time licking into Deans mouth, tasting smoke and beer

Flicking the cigarette away, Deans hands grabbed the other mans hips and pulled them flush against his own. He panted into Cas' mouth as he felt the outline of his hardening cock press against his own.

Castiel's hand snaked down Deans waist and made quick work of the skinny leather belt in his way. He plunged his hand inside, trailing his fingers over Dean's boxer briefs.

Dean let his head thump back against the solid brick behind him, panting into the sky.

"Cas," he whispered before his lips were captured by Castiel's. He sucked them roughly, tightening his grip on Dean's cock. Dean grunted as his hands flew up to grip the sides of Cas' head, fingers roughly tugging his thick hair.

Castiel relinquished his grip and slipped his hand inside Dean's boxers, finally getting a proper grip on him. He stroked him hard and fast, tongue flicking out to lick Dean's lips.

"Fuck," Dean moaned loudly, his eyes opening to see Castiel watching him intently. The older man smirked before Dean saw his blue eyes flick somewhere off in the distance, then back to him.

Castiel bit Dean's lip once more before shifting his weight, one hand still roughly jerking his cock, the other reaching behind himself.

Through his daze, Dean saw Castiel's coat flare out behind him. He pulled something shiny out and Dean watched as Castiel stretched his arm out to the side. His eyes never left Deans, his hand never stopped stroking.

Dean turned his head, following Castiel's arm. A gasp caught in his throat when he saw Ruby approaching with a knife drawn.

"Cas," Dean shouted.

Castiel tightened his grip and stroked him fast, bringing Dean to the edge of his orgasm. He bit down on the side of Dean's neck and thumbed the slit of his cock.

Dean heard a muted gunshot. He eyes widened as he came in Castiel's hand the same time he watched Ruby fall lifelessly to the ground with a bullet hole between her eyes.


	6. Chapter 6

**Summary for the Chapter:**

> Dean learns what Castiel does for a living.

Panting with eyes wide and blurry, Dean stared at the body laying on the lawn.

"Cas what the FUCK!" He vaguely feels the man remove his hand from his pants and buckle his belt. He tore his eyes away from the pool of blood surrounding the girl that was hitting on him less than an hour ago to look at Cas. He's frighteningly calm as he tucks Dean's shirt into his pants. Cas glances up at Dean before putting his gun away and pulling out his phone.

"Back yard, in the garden....just one...keep your eyes down, on the body only." He stuffed it in his pocket and reached up to cradle Dean's face. "Are you alright?"

Dean smacked his hand away and tried to move but his feet feel like they're cemented to the ground.

"What. The. FU--," Dean starts to yell, but is muffled by Cas' hand slamming over his mouth, fingers splayed against his cheek while the mans thumb digs into the soft spot of his jaw. His eyes water and his heart is pounding in his ears. He tries to pull away but Cas has a death grip on his face. He considers biting the webbing between the mans thumb and pointer finger but thinks better of it, the guy has a gun after all.

"I understand you're upset," Castiel whispered, "and this certainly isn't the way I wanted you to find out about my line of work."

Dean looks anywhere but the mans face. Tears spill over his cheeks as he stares up into the sky, watching dark clouds loom overhead.

A noise caught his attention but he didn't dare look. He could see two shapes move in his peripheral vision, then the distinct sound of something being dragged away. His chest heaved as more tears sprung from his eyes, little spots starting to dance around in his eyes.

"Dean, you're hyperventilating. I need you to breathe, can you do that for me?" His blue eyes softened as he took a deep breath, watching as Dean's shoulders rose along with his. "I'm going to remove my hand now. Try to not scream again." He moved his hand from Dean's mouth to the side of his neck. "Breathe, Dean."

Dean slumped forward with his hands on his knees and sucked air into his burning lungs. He looked up at Castiel through his wet lashes and wiped away tears and snot from his face.

"Why," he gasped, "why'd you kill Ruby?"

Castiel pulled his eyebrows together. "You knew her?"

Dean sucked in a few more breaths before throwing his arm out to the side. "She was the one hitting on me at the bar."

"She spoke to you?" Castiel hauled Dean upright, hands gripping the collar of his suit jacket. "What did she say?"

Dean froze in place, his mouth opening and closing. "Cas, you're scarin' me," he whispered.

Nostrils flaring, Castiel let go of Dean and took a step back. He noticed a few people heading in their direction, smoke billowing from their lips.

"Perhaps we should take this somewhere else. Michelle will need to know the job is done, and you'll need to speak with her as well. Come," he held out his hand for Dean to take.

Watching Dean recoil hit Cas in the gut like a sucker punch. He softened his eyes and his tone. "Dean, please come with me. I'll explain everything. I swear."

Dean looked down to the mans waiting hand.

"For appearances sake," Castiel pleaded. Dean reached out his trembling hand and wiped at his face with the other, trying to make it look like he didn't just witness a murder. They walked in silence through the house until they reached Michelle's office. Castiel didn't bother to knock, instead he shoved the door open and dragged Dean in behind him.

"Castiel," Michelle smiled around the woman sitting in her lap, "ever heard of knocking?" She raised an eyebrow and licked her lips, returning her attention to the woman. "Sadly, we'll have to continue this another time, my sweet." Michelle straightened the woman's dress strap and helped her off her lap. She bent over, disappearing behind the desk for a moment before standing again. Her face was flushed as she passed by Dean and Castiel, stuffing a pair of red panties into her purse.

Castiel waited until he heard the door shut before ushering Dean further into the room, making him sit in the leather chair.

Michelle leaned forward on the desk and laced her fingers. "What is so important that I needed to send away my anniversary present?"

"It's done," he stated. "Dean--was there," he sighed.

"Ok," she glanced to Dean then back to Castiel. "Anything else?"

"She spoke to Dean." Castiel's jaw set in a hard line as he white knuckled the back of Dean's chair.

Michelle's eyes widened for a split second. She turned her gaze to Dean. "What exactly did she say to you, Dean?" she asked softly, clearly seeing he was ready to bolt out of the room at any moment.

Dean looked up to Castiel who pressed his lips together and nodded. "She uh---came up to me at the bar while you 'n Cas were having your meeting." He cleared his throat and narrowed his eyes, thinking back. "I thought it was Cas comin' up behind me so I turned around and she started flirting with me. Said she'd never seen anyone with Cas at these parties before," he looked up again and offered Cas a weak smile. "Asked for my name and said he hoped to see me around, and that was it. She didn't even drink the beer she ordered," he added as an after thought.

Michelle chewed her lips and sighed.

"Sorry, that's---it's all I remember. She didn't stick around---"

Dean felt Castiel's hand slide over his shoulder, rubbing gently. "You did great Dean. Thank you."

He looked over to Michelle. "Who was she? Why's it such a big deal that she talked to me? I mean, I get hit on all the time, not like she needed to be shot in the fuckin' head for it." 

He felt Castiel bristle behind him as Michelle huffed a laugh through her nose. She reached over and pulled on the top of a silver canister, revealing a compartment of cigarettes. "Do you smoke Dean?" she offered, gesturing to the canister.

"Not usually but I sure as fuck could use one after what I just saw."

Castiel walked from behind the chair and plucked one out, lighting it with the help of Michelle's matchbook. He took a long drag and blew it out before handing it to Dean. It trembled between his fingers as he sat forward, elbows on his knees.

"Ruby works for a team of assassins that rival our own. She hasn't been seen in years, always looks different. Changes her hair, her eye color, weight and what have you," Michelle tossed a hand in the air. "That's the reason I threw this ridiculous party. I was hoping to flush her out."

Dean stared at the floor for a long moment before bringing the cigarette to his lips. He held it until his lungs burned then exhaled. "So you're sayin'," he swallowed thickly looking up to Michelle, pointing at her with the cigarette, "you guys are some group of killers and I was essentially the bait tonight?"

"No, Dean. You were never bait," Castiel assured him. He knelt down in front of Dean and splayed his hands over the mans thighs. "We are--," Cas sighed and looked to Michelle who shrugged, her expression non committal. He took a deep breath and tipped Deans chin up with one finger. "My business, the work I do, it's for Michelle. I'm her soldier and she's the Capo of Kansas."

"Capo," Dean scoffed, taking another drag. "The fuck does that mean?"

"It means she's the head of the mafia in this state," Castiel clarified. He eyed Dean's trembling hands and removed the cigarette from between his fingers. "She hands out orders, and people like me make sure they're taken care of."

Dean pressed his lips together and tipped his head back, sighing. "Oh, you've gotta be fucking kidding me," he whispered to himself.

"I'm afraid not, Dean," Michelle said as she snuffed out her cigarette. "And after tonight, you're a part of this now."

"You have to believe me when I say I didn't want you to find out like this," Castiel tightened his grip on Dean's thighs.

"What do you know about your father, Dean?" Michelle asked out of the blue.

Dean narrowed his eyes and shot the woman a glare. "Why the fuck would you ask me that?"

Castiel eyebrows shot up as he raised a hand in the air and shook his head quickly. Michelle slowly rose from her seat and braced herself on the desk, leaning in towards the men. "I'd mind my tone if I were you, boy."

Her voice sent ice through Dean's veins, his eyes glued to her hardened face. "He died right after Samm---my brother was born. Died in a fire," he answered in a shaky voice.

Castiel stood, rolling his shoulders back. "Do you have it?" he asked Michelle.

"I do, but he's not ready," she said crossing her arms. "Wait until everything has calmed down and we'll talk then, Dean." Her eyes flicked to the door then to Castiel, indicating that the meeting was over.

"Come on, Dean. Let's go." He helped Dean stand and walked him out of the room.

The drive home was tense. Castiel glanced at Dean every thirty seconds which was really getting on Dean's nerves. Tears stung the back of his eyes as he stared out the window into the night but he would be damned if he cried in front of Cas again.

They pulled up to Castiel's mansion and exited the car in silence. The older man ushered Dean in, his hand gently resting on his lower back. He wordlessly led Dean up the staircase and into a room Dean had never seen before.

"My room," Castiel explained. He pulled off his suit coat and popped the buttons of his shirt. Dean stood there unmoving, taking in his surroundings. He watched as Castiel removed the gun from the back of his pants and laid it on the bedside table. Castiel looked over his shoulder at the statue of a man behind him and sighed.

"I know a lot happened tonight, and you'll need time to process everything, but if it's not too much to ask I'd like you to stay here with me tonight."

Dean shrugged. "Like I have a choice." His eyes felt heavy and his chest ached. The adrenaline was no longer coursing through his veins and he felt like he was hit by a semi.

A wave of sadness washed over Castiels' face. "Of course you have a choice. I would be lying if I said it wasn't for my benefit as well, but Dean, I'd really like to take care of you tonight." He walked over and helped Dean shrug off his jacket, tossing it onto a nearby chair. His hand reached up to cradle the other mans face. "I'm so sorry for the way things happened tonight."

Dean shrugged again which made Castiel sigh and lower his head. He swallowed thickly before leaning into Castiel a little more. "I'd like a shower if that's alright."

That made Castiel perk up. He lifted his head and smiled. "Y-yes, yes of course," he stammered, clearly jumping at the chance to do anything Dean wanted. He tugged Deans hand and pulled him into an adjoining room and flipped on the lights.

A massive claw foot tub sat in the center of the room with end tables surrounding it. There were baskets of rolled towels and washcloths, others had glass bottles of soap and oils. The shower took up the entire back wall and had three different shower heads hanging from the ceiling.

"On second thought," he nodded towards the tub.

Castiel nodded once and kissed Dean so quickly on the cheek Dean wasn't sure he even made contact. He walked over to the tub and turned the handles, testing the water until he deemed it suitable. He returned to Dean's side and began unbuttoning the mans shirt, dropping it to the floor when he finished. Dean stood there in a sleepy haze as Castiel continued undressing him, too out of it to care that he was now standing naked, for the first time, in front of Castiel.

Castiel undressed himself quickly and reached out to take Dean's hand, slowly guiding him to the tub. He eased Dean in before stepping in behind him, his hands immediately working the knots out of Dean's shoulders. He bathed Dean with a soft sponge with soap that smelled like lavender, letting the water drip down his chest and back.

Once Dean was feeling relaxed, he leaned back against Castiel and straightened his legs out with a groan. His eyes refused to open, his body felt like it weighed a ton so he sunk deeper into the tub, feeling the water hit his chin.

"You're in the mob," Dean said groggily, barely above a whisper.

That's the last thing he remembers before succumbing to exhaustion.


	7. Chapter 7

**Summary for the Chapter:**

> Dean gets a rundown of what is expected of him now that he's Mafia by proxy.  
***Warning: Smutty goodness in this chapter***

The first thing that registered to Dean was warmth.

He frowned, pinching his eyes together, trying to savor the few moments between sleep and being awake. He shoved his arm under the pillow and buried his face into the silk pillow case, sighing as something soft ran up and down his back.

Then his eyes shot open. He twisted and sat up, staring at Castiel.

"Good morning," Castiel said, his face frustratingly neutral.

"Morning," Dean mumbled, pulling the blanket tight around his waist.

Castiel rolled his eyes and swung his feet over the edge of the bed. "Little late for modesty," he chuckled.

Dean scratched his head and yawned. "I uh, I don't remember---how did---," he stammered while looking around the room. His suit from last night was hung on the back of the door with his shoes below, his wallet and phone placed on the end table nearest him.

"You fell asleep in the tub. I carried you to bed," Castiel answered Dean's vague attempt at a question while lifting a silver coffee pot of a cart on the other side of the room. He filled two cups, balancing them in one hand while he carried over a covered tray.

"You---carried me. And put me to bed." Dean reached out and took one of the cups from Castiel.

"Yes?" Castiel raised an eyebrow while taking a long sip of coffee.

Dean started at the black liquid in his cup before shrugging and taking a drink. He sighed and leaned his head against the soft headboard. "Ok."

"I'm not sure what you eat for breakfast so I had the cook make a little of everything." Castiel took the cover off the tray, revealing bacon, eggs, toast, waffles and fruit that Dean pointedly ignored.

"Jesus, Cas," Dean scoffed while taking a piece of bacon, "you didn't have to. I usually just have this," he lifted his cup.

Castiel frowned, looking down at his steaming cup.

"B-but thank you," Dean added quickly. "I never turn down a good slice of bacon." He stuffed the whole piece in his mouth and chewed obnoxiously loud.

Castiel huffed a laugh through his nose and smiled. "I guess it's--I'm still trying to apologize."

Dean shrugged. "You're off to a good start." He grabbed a waffle and bit into it, ripping it in half.

"I've provided you with utensils, Dean," Castiel chided. Dean replied with a smile, his cheeks sticking out like a chipmunk.

"Last night was--for lack of a better word, insightful. For me at least." He looked to Dean who's smile was fading and turned to face him, taking his non syrupy hand. "If anyone else saw what happened last night as up close and personal as you did, I would be forced to remedy that situation as well." Castiel lowered his head to catch Dean's eye line. "Do you understand?"

Dean gulped down the waffle in his mouth and nodded. "You'd---you'd have to kill them, too."

"Yes," Castiel squeezed Dean's hand lightly. "But with you--," he sighed and ran a hand through his hair, making his bedhead even worse, "I just--I thought you might---I'm sorry if--"

"Cas, stop." Dean moved the plate off his lap and set his coffee down. He took the other mans face in his hands, syrup be damned, and looked him in the eye. "Yeah, last night was fuckin' weird and scary and there were about three different times I wanted to throw up. But I think," he paused and licked his lips, taking a deep breath, "I think somehow, I kinda knew, y'know? The money, the cars that follow you around. Like I said, you aren't exactly subtle."

Castiel covered Dean's hand with his own and sighed. "It _is _subtle though, Dean. To everyone else. To normal people."

Dean scoffed, rubbing his thumb over Cas' cheek. "Then how come I noticed?" he asked cockily.

Castiel's frowned deeper and patted Deans hand before pulling it away. "I have some things to tell you, and you---you're probably going to be very upset about them, but it will help you understand. And if at the end of the discussion you want to walk away from this," he gestured between them, "I'll understand."

Dean's mouth opened and closed multiple times before he finally nodded.

"Ok. There are clothes for you in the dresser. I'll be in the study." He kissed Dean gently on the cheek before leaving the room.

Dean sat there for a while staring at the cooling eggs on his plate. He should be freaked out. He should be running to the police station screaming "My boyfriend is in the mafia!". But after processing last night, he was strangely calm. He finished his coffee an got dressed, impressed with the selection of clothing Castiel had provided. Then it hit him-

He had _no _idea where the study was. He walked down the hallway that he vaguely remembers from last night, stopping to look at the portraits hanging on the walls. They were mostly old men, each dressed in a nice suit with angry expressions on their faces. That is, until he got to the end of the hall.

A full length portrait of Michelle in a bright red dress standing in front of her desk took up almost the entire space between the floor and ceiling. He looked back and forth between her picture and the men's. Dean huffed as it dawned on him. They must have been all the other Capos before her. Which might make the very angry man in Castiel and Michelle's home the _Boss' _boss. The word "Godfather" bounced around in Dean's head as he continued looking for the study, but he was pretty sure that was made up for the movies.

He heard Castiel's voice coming from a room and pushed the door open. It looked almost exactly like Michelle's room last night, except Castiel had a giant fireplace behind his desk and a statue of a man's bust next to it.

Castiel held up one finger to his mouth, signaling Dean to be quiet as he talked on the phone. He closed the door quietly and walked up to Castiel's desk, pulling a folder that read "Winchester" towards him with one finger.

"Yes....I have it...what's his clearance?," he glanced at Dean and then down to the folder, "Tell Michelle I want it raised. She knows who----I don't care. _You're_ an associate, Dean blew past that last night...fuck. Fine. Set up a phone call with her as soon as possible for me." He slammed his phone on the desk with a smack and sighed, pinching the bridge of his nose.

"Everything ok," Dean asked, tapping on the folder.

"Not really, and yet, here we are," he gestured vaguely. "Have a seat."

Just to be a little shit, Dean rounded the desk and sat in Castiel's plush leather chair. Castiel huffed and smiled, running a hand over his mouth. He stood next to Dean and flipped the folder open.

Dean's heart plummeted into his stomach. For the fourth time in twenty four hours he felt like he was going to throw up. He picked up a photo and swallowed thickly.

"How did--," he looked up at Castiel, "why the fuck do you have pictures of my dad." He shoved the folder away and stood quickly, the chair scraping loudly across the floor.

"John---"

"DON'T say his name," Dean pointed a finger in the other man's face, "don't you dare."

Castiel braced himself on the desk and turned the folder sideways so Dean could see it. "He worked for the old Capo, the one Michelle took over for," he explained.

"No. No-no-no-no. My dad was a mechanic. He---he fixed fucking cars for a living," Dean shouted. "He was a piece of shit father who left my mom and his son's to fend for themselves. Sam was a fucking _baby._ He never even knew him!"

"Dean please calm down," Castiel held up his hands and slowly approached him.

"No," Dean backed away. "No. You're wrong. That's not---," he shook his head and pointed to the picture of his dad in the Impala.

"Dean, think about it. How were you able to spot my security car so easily? Remember? You said 'they stick out like a sore thumb to a guy like you'? You were sitting up in bed not twenty minutes ago enjoying your breakfast after watching a woman die like nothing happened."

Dean crossed his arms and looked down, still shaking his head.

"How many exits are in this room," Castiel asked randomly.

"Three," Dean answered immediately. His head shot up and started at Castiel. "I didn't--how'd---"

Castiel walked up to Dean biting back a smile. "You were born into this, Dean. Whether you remember it or not, Joh--," Dean glared at the man, "your father ingrained these things into your head at a young age. He took you hunting, correct?"

"Yeah all the time," he mumbled. "Said I needed to know how to field dress and skin a deer. Said all men---," he stopped and tilted his head. "He said---"

Castiel reached out and held Dean's shaking hands. "He was grooming you."

Dean's eyes watered. His heart was pounding in his ears.

"Breathe, Dean," Castiel whispered. He laid a hand on Dean's chest, feeling him take in a deep breath. "Good. Now, when you're ready, we can discuss it more."

"M'ready. Just---let's get this over with," he mumbled. He walked over and sat back down in Cas' chair, roughly pulling the folder in front of him. He flipped the picture of his dad over and slid it to the side. There were papers detailing most aspects of what John's job entailed, the hits he was ordered to make, and a list of something called a DNH. Deans finger slid over the abbreviation.

"Do not harm," Castiel explained.

Deans eyes scanned the list, seeing names he didn't recognize until he reached the bottom.

  * Samuel Campbell
  * Deana Campbell
  * Mary Campbell-Winchester
  * Dean Winchester
  * Sam Winchester <strike>(not yet born)</strike>
  * Bobby Singer

Dean ran a hand over his mouth as he sighed. "Did you know?"

"I suspected," Castiel admitted. "Gabriel is---he's an associate. I've known him for a very long time and when he mentioned someone with the name Winchester was working with him and I had to see. You're father may not have been a good man, but he was a great soldier."

Dean snorted and continued shuffling through the papers. There was a photo of a charred building with the Impala parked in the alley beside it.

"Is this," Dean looked up to Castiel who nodded.

"It was a hit. The family Ruby works--worked for issued it when he was closing in on their territory. He was ordered to find their Don and take him out." Castiel squeezed Dean's shoulder lightly.

"So you're saying, this other family--"

"The Romans," Castiel offered.

"They killed my dad?"

Castiel nodded somberly. "I'm sorry. I never should have pulled you into this."

"Was any of it real?" Dean stood and crossed his arms.

"Was what---"

"You and me. The 'void' in your life or whatever. You found out who I was and you wanted me to, what? Pay me to stay with you so you could keep an eye on me?" Dean shoved hard against Castiel's chest.

"No, Dean, no," Castiel spoke slowly, holding his hands up. "I--"

"Why should I believe a fucking word you say," Dean shouted, pushing him again, enough to make Castiel stumble back.

Castiel let his arms drop to his sides.

"Come on!" Dean yelled, balling his fists. "Fight back!" Tears pricked his eyes and threatened to spill over.

Castiel saw it before Dean probably even registered what he was doing.

Deans fist cut through the air heading directly towards Cas' jaw. He caught Dean's hand and directed it to the side, shoving it down and twisting it behind Dean's back. He threw him over his desk, smashing the younger mans face into the folder he was just reading.

"Is this what you want?" Castiel growled. When Dean didn't answer, he yanked his arm higher up on his back, making Dean howl in pain.

Dean panted against the table, tears springing from his eyes.

"I asked you a question," Castiel reminded him.

Dean could feel Castiel getting hard against his ass. He pressed back, pretending to struggle. A growl bubbled from Cas' throat as he gripped Dean's hip with his other hand, digging his fingers in.

"Yes," Dean hissed.

Castiel's nostrils flared. He let go of Deans hip and quickly unbuckled his belt, shoving his pants down around his thighs. Dean reached between himself and the table to unbutton his pants, letting Castiel rip them down over his ass.

Castiel sighed heavily as he bent forward, folding himself onto Dean and stuffed two fingers in Dean's mouth, gripping his chin tight with his thumb. He sucked immediately, twisting his tongue around them. Castiel shoved them in deeper, teasing the back of his throat. He ripped them out, feeling Dean's teeth scrape across them. He tightened his grip on Deans bent arm as he slid his slick fingers between the mans cheeks, teasing at his hole.

Dean pinched his eyes shut and rutted against the table as Castiel worked him open. His free hand white knuckled the desk as Castiel grazed his prostate.

"It seems," Castiel growled while watching his fingers pump in and out, "you need to be taught your place." He scissored his fingers, making Dean twitch and lift off the table. Castiel slammed him back down by his twisted arm. "You may be part of this now, Dean, but you are far from privileged."

He removed his fingers and stroked his own cock a few times before lining up to Dean. He pushed inside with a grunt, setting a hard and fast rhythm.

Dean cried out and gasped at anything he could get his hands on. He balled the folders papers in his fists, pressing his forehead hard against the desk.

"Fuck, Dean," Castiel growled as he pounded into Dean until he felt his orgasm building. He bent forward and jerked Dean's length in time with his thrusts, breathing heavily on the younger mans back.

Dean cried out when Castiel's cock pounded into his prostate, immediately coming into Cas' hand and down the side of the desk. With a cocky smirk, Castiel lifted his fingers to Dean's lips and teased them open. He dragged them over Dean's tongue, feeling him lick at them greedily. Castiel fucked into him hard, shouting as he came inside Dean's fucked out hole.

Slowly, he released Deans arm, helping him straighten it out. He pulled himself out of Dean and tucked himself into his boxers, zipping his pants up afterwards. He pulled at Deans hips, signaling him to stand. Dean slowly rose off the desk, wincing at the pain in his arm as he rotated his shoulder a few times. He turned around, red faced and panting.

Castiel looked down, noticing the state of Dean's pants, and tucked him away as well.

"Are you alright," Castiel asked, his voice full of concern. "I---I got carried away, I apologize." He reached up and gently rubbed Dean's shoulder.

"S'fine," he shrugged. "Should've have tried to punch you." 

"No, you shouldn't have. But I shouldn't have done this, either," he gestured towards Dean's shoulder. He let his hand fall to Dean's hand and squeezed it tightly. "You're lucky it was just me, though. I thought Michelle was going to stab you last night when you swore at her," he chuckled.

Dean raised his eyebrows, eyed blown wide. "She wouldn---"

"She would," Castiel raised an eyebrow with a smile. He reached up and caressed Dean's face. "You have a lot to learn in a very short amount of time, Dean. I have to talk to Michelle and convince her to promote you to soldier instead of a ridiculous associate," he spat, "and then our work can begin."

"W-what work," Dean's face twisted with confusion.

"We're going hunting."


	8. Chapter 8

"Is there a rule or something that once you join the mob you have to dress like this?" Dean wriggled in his blue pinstriped suit coat. "Do you have any _idea _how cliche this is?"

Castiel rolled his eyes as he fixed Dean's collar. "You aren't 'in the mob'," he air quoted which made Dean snort. "We don't call it that."

"But that's exactly what this is, isn't it?" Dean batted Cas' hand away and tugged on the sides of his coat, checking himself out in the mirror.

Castiel walked up behind Dean and slipped his arms around his waist, mentally noting that they looked absolutely sinful together like this. He nuzzled his nose into Deans neck and whispered "Think of it as a very large family with an extraordinary amount of money that take care of each other. And when they don't," he raised his finger to Deans throat and slid it across slowly. Dean raised an eyebrow, spinning in Cas' arms. He reached up, gripping the side of Castiel's neck and kissed him briefly on the lips.

"Dean, good to see you again," Michelle smiled. "I trust we've had time to explain things?" The men walked into Michelle's office together and approached her desk.

"We have," Castiel answered, his eyes flicking to Dean.

"Wonderful." He clapped her hands together and looked to Dean. "Castiel tells me you'd like to be more involved. You're aware of what this entails?"

Dean squared his shoulders. "I do." And I am.

Michelle squinted her eyes and smirked. "I really hope you do, Dean. It would be such a waste of pure talent if you changed your mind."

He thought back to this morning when Castiel showed him what happens when you don't do as your told in this family.

"Michelle, is this really nessec--" Castiel was cut off by Dean holding up a hand.

"I understand the risks and what I'm getting myself into. Just because I don't have murder notches on my belt doesn't mean I can't be a good soldier for you, which is why we came here today. I need at least Castiel's level of clearance. I fully intent to be with him for however long he sees fit and would like to accompany him on future jobs." He took a deep breath and looked over to a very wide eyed Castiel. "No better way to learn than on the job," he clarified with a smile.

Michelle sat back and crossed her arms, a smile creeping across her face. "Oh, I like him, Castiel." She licked her lips and looked thoughtful for a moment while staring at Dean. "Your name alone qualifies you to join the family ranks but you have to make it worth my while. Your father," Dean bristled at the mention of him, "was---a marvel," she shook her head with a knowing smile, "the things that man could do with a knife. You have big shoes to fill, Dean. Don't disappoint me."

"Thank you, ma'am. I won't let you down." Dean bit his cheek to stop himself from smiling.

Michelle scoffed. "Do I look like a _ma'am_ to you? Call me Michelle."

The phone on her desk rang and she held up a finger to the men. Dean beamed over at Castiel who was visibly bursting with pride.

"Just wait until I get you home," Castiel growled, tugging Dean closer. Dean's cheeks flushed immediately glancing over to Michelle who rolled her eyes.

"Yeah? You gonna take care of your soldier, Cas?" Dean whispered.

"That will have to wait," Michelle interrupted. "I have a job for you two."

The alley was quiet as they sat in the car. Dean watched as Castiel stared out the window, eyeing every person who walked past.

"So what did this guy do?" Dean asked, slinking down in his seat. The tiny Camry had nothing on the Impalas bench seat, but it didn't exactly blend in so he was forced to ride in this piece of crap.

Castiel leaned his back against the headrest. "He's been skimming off the top of the product he sells."

"Wait," Dean sat up in his seat and stared at the other man. "You---you guys sell drugs?"

Castiel huffed through his nose and smirked. "Not drugs. Michelle put an end to that. One of the many reasons she's better than the old Capo. Guns on the other hand," Castiel shrugged.

"So he's your gun runner and he's taking what, a few hundred off the top?" Dean guessed.

"More like a few thousand," Castiel corrected.

"Shit," Dean hissed. "Should probably teach him a lesson."

Castiel licked his lips as he watched Dean wink. "I must say, I'm absolutely obsessed with watching you slip so easily into the lifestyle." He ran a finger along Dean's jawline. "It's fascinating."

Dean ducked his head and blushed, thankful the darkness of the alley hid it. Castiel pulled his hand away and stiffened. "There he is," he whispered as he pulled a gun out of his waistband. Dean looked across the street to and saw a man coming out of a pawn shop. "Stay here," Castiel demanded.

He got out of the car and walked towards the man with his gun held behind his back, approaching him with a wave and a smile. Dean couldn't tell what they were saying but it seemed as if Castiel was asking him for directions. Cas hooked his thumb over his shoulder and asked a question, tilting his head to the side. The man shook his head and pointed the other way with a smile. Castiel nodded and reached out his hand. When he took it, Castiel yanked him in close, pointing the gun at the mans stomach. Castiel's eyebrows lowered as he spoke, tugging the man roughly again. The man nodded shakily as Castiel shoved him forward, pointing towards the alley.

Dean watched as the man looked back at Castiel before taking off like a rocket, running directly towards their car. He was approaching the car fast, and without thinking, Dean kicked open his door, slamming it into the mans chest and knees. He fell face first to the ground groaning, reaching for something behind his back. Dean jumped out of the car and stomped on the mans back, holding him down.

"I wouldn't do that if I were you," he growled, reaching down and grabbing the mans gun and tossing it into a nearby dumpster. Castiel jogged up to see Dean holding the man down and smiled briefly.

"Get him in the back," he ordered, tossing a pair of handcuffs at Dean.

Dean knelt down and cuffed him, pulling him up by his restraints. He threw him in the back of the car before climbing into the front seat.

"Watch him," Castiel whispered, sliding his gun across the seat. Dean picked it up and twisted his body so he was facing the backseat. Castiel revved the engine and squealed the tires, jetting out into the street.

"Please, I don't know what this is about," the man sniveled. Castiel looked at him through the rear view mirror and raised an eyebrow. "I'm serious, I'll give you my wallet, my phone, anything! Please just let me go! I won't tell the cops anything!"

"Shut. Up." Castiel growled. Dean raised the gun, resting it on the side of the seat just enough so the guy could see it.

"Jesus, oh God, please. Please let me go! I don't even know you people. I swear I won't tell!" he screamed, struggling against his restraints. Castiel looked at Dean and gestured towards the man with a nod of his head. Dean fully turned around in his seat and reared back before punching the man hard in the face, effectively knocking him out.

"I meant shoot him, but I guess that works too," Castiel smirked.

They drove across town to a warehouse at the end of a pier. Dean got out of the car and watched the water lap onto the shore, enjoying the lights dancing off the water before opening the backdoor. He hauled the still unconscious man out of the car, lifting him over his shoulder easily as Castiel unlocked the warehouse door. He swung it open and ushered Dean in, keeping his eye out for anyone that might be watching.

"Tie him up," Castiel ordered, gesturing to a metal chair in the middle of the room. Dean dumped the man in the seat and walked over to a table that had cable ties on it. He twisted the ties over the mans wrists and secured them tightly to the arm rests of the chair, tugging on them hard to make sure he couldn't get out.

Castiel removed his suit jacket and rolled up his sleeves slowly, eyeing the man in the chair. "Wake him up."

Dean stood in front of the man and slapped him hard across the face. His head jerked up as his eyes flew open.

"Fuck, no, God. Please let me go," the man begged.

"Shut up, Alfie," Castiel growled.

Both Dean and the man's eyebrows shot up.

"I don't---how do---who are you?" Aflie stammered.

"Michelle sent us," Castiel clarified.

Alfie sniffed and straightened his posture, immediately changing his attitude. "Ah, shit," he grumbled. "So that makes you--," Alfie raised an eyebrow.

"Castiel Novak."

"Oh fuck," Alfie sighed, lowering his head. His hands shook so hard the chair rattled and his eyes brimmed with tears.

Dean looked in awe at the man. The mere _mention _of Cas' name shook the guy to his core.

Castiel approached Alfie, towering over him as he gripped the mans jaw tight and pulled his face up to meet his eye line. "You've disrespected the family, Alfie. You've disrespected yourself. Are we not good to you? Do we not take care of you?"

Alfie tensed his jaw, glaring at Castiel.

"All we want to know is why," Castiel explained, loosening his grip.

"You stupid soldiers," he spat. "You don't know what it's like. Runners make _nothing_ compared you."

Castiel took a step back. "If it's an issue of pay you could always talk to Michelle. She's very generous."

Dean cocked his head to the side, watching Alfie's face split into a grin, teeth red with blood.

"Fuck Michelle," he laughed. "That bitch can rot in hell for all I care. There's a new Capo in town and it's not that slut."

Dean stepped up next to Castiel. "Who're you working for," he asked crossing his arms.

Alfie side-eyed Dean. "Why would I tell you? Who the fuck are you, anyway?"

Dean raised his chin and smiled. "John Winchesters son, Dean." Alfie visibly swallowed hard, his Adam's apple twitching. "So, we gonna do this the easy way and answer our questions," Dean bent down and stared at the man, "or we gonna do this the hard way?"

Alfie set his jaw as his nostrils flared, avoiding eye contact with either of the men in front of him.

"Hard way it is," Castiel sighed. He shoved his sleeves up higher and walked over to a rickety table, throwing off a sheet that covered its contents. His fingers skimmed over a variety of weapons until he landed on an ice pick. He spun it between his fingers before handing it to Dean.

Dean swallowed hard as he took it from Castiel. He looked Alfie over before settling his gaze on his fingers. "Last chance," he offered.

Alfie slowly turned his head to Dean, eyes bloodshot and watery. "Fuck. You."

Dean clicked his tongue as he walked forward. He set the sharp tip of the ice pick at the base of Alfie's cuticle on his middle finger. He tried squirming away but the cable ties held him in place. Dean looked into the mans eyes as he applied pressure there, watching his nail turn from pink to white. He raised his eyebrows questioningly to Alfie. He tipped his head back and spit in Dean's face.

Dean closed his eyes and chuckled while wiping his cheek off on his shoulder. He held the ice pick in one hand, pressing down and balled his other hand. He lifted his fist above his head and slammed it down on the ice picks handle, piercing through Alfie's finger.

He screamed out and pulled against the ties, tears streaming down his face.

Dean knelt down and took the mans face in his free hand, squeezing roughly on both cheeks. "Nine more to go before I start working on other parts of your body."

Alfie whipped his head to the side, breaking Dean's hold on his face but said nothing.

"Alright," Dean grunted as he stood, looking back at Castiel who nodded. Dean plucked the ice pick out of the man's finger and placed it on his ring finger in the same spot. Fist raised, he started swinging it down.

"Wait!" Alfie screamed. Dean froze, hand mid air. "Wait," he panted. Dean dropped his hand but still held pressure on the pick. Alfie looked to Castiel and sighed. "Someone approached me last month, didn't know who he was. He said he was looking for information on Michelle. I told him to fuck off at first but three other guys came outta nowhere and---," he closed his eyes and shook his head. "They said they'd buy the guns cheap and I could skim the rest in return for tabs on her."

"So you're selling the Romans our weapons, getting rich off the profits _and _ratting on our Capo," Castiel clarified. He ran a hand down his face and sighed heavily. "You realize what this means, Alfie."

The man lifted his head slowly. "Damage is already done. It won't matter if you kill me." He turned to Dean and faked a pout. "Poor baby boy, you have no idea what you've gotten yourself into." He turned to Castiel and squared his shoulders, lungs sucking in their last breaths. "Make it quick," he hissed to Castiel.

Castiel held out his hand to Dean, eyeing the ice pick. Dean handed it to him with wide eyes. He spun it in his palm as he stalked up to Alfie, watching the mans eyes widen. He leaned forward, bracing himself with one hand on the chair and rested his forehead against the other mans. For a moment, it was quiet, the only sound in the room was their breathing and the far waves crashing into the shore. Castiel's arm shifted forward, plunging the ice pick straight through Alfies heart. He grimaced and jerked against the chair as blood bubbled up into his throat. Castiel closed his eyes and twisted the pick before pulling it out, keeping his head resting against Alfies. The boy slumped, his dead weight pressing against Castiel's chest as blood poured from his mouth onto the man's crisp white shirt.

It was strangely beautiful to Dean. He watched an awe as Castiel leaned up and kissed Alfie tenderly on his forehead before dropping the pick to the floor. He pulled out his phone and hit a button.

"Warehouse 7," was all he said before stuffing his phone back in his pocket. He walked over to the table and wiped his hands on the sheet before picking up his jacket. He looked to Dean and straightened the collar.

"Ready to go home? The cook is making meatloaf tonight."


	9. Chapter 9

**Summary for the Chapter:**

> Cas and Dean never wind up eating meatloaf.  
Castiel informs Michelle of the rat and decide what to do about it.  
Cas and Dean talk about their relationship.
> 
> I've been having a very hard time coming up with the next part of this story. If you didn't know, I don't have a rough draft or outline for stories I write, they just kind of come to me in dreams and it goes wherever the story leads.  
Thanks for sticking with me so far and I hope you enjoy!

"Jesus Christ, Cas," Dean panted. He tried to raise his hips but Castiel kept him locked in place with his forearm, pressing down hard on the top of his thighs. He was completely at the other mans mercy as he swallowed him down. Dean balled the sheet in his fists and cursed under his breath. He looked down at the mass of black hair and pink lips between his legs and groaned.

"Fuck yes," he hissed, taking hold of Cas' hair. "Suck my fucking cock, Cas. Fuck. Fuckfucfuc---" he shouted as he felt his orgasm rip through him. He folded in on himself, leaning up and keeping Castiel's mouth pressed against his groin. He reached down and pressed his hand to Cas' cheek, feeling his cock through the stubble.

"Jesus," Dean sighed heavily, watching as Castiel looked up at him through his lashes with a wicked grin. He fell back on the bed as Castiel released him, lips slick with spit and come.

He vaguely registered Castiel work his way up his body, feeling the mans lips graze against his chest and neck. He laid there in complete bliss as Castiel lined himself with Deans' loose hole and pressed inside with a groan. He gripped the back of Deans neck and squeezed lightly.

"Open your eyes baby," Castiel whispered. He watched as Dean obeyed, smiling when his green eyes focused on his face. He pushed in deep and licked his lips as Deans eyes widened. "Do you have any idea how proud I am of you? How fascinating it is," he sighed, his hips stuttering slightly, "watching you do what you were born to do?"

Dean smiled and lifted his hips up, meeting Castiel's quickening pace. "Yeah? You like watchin' me work, Cas?"

Castiel lowered his head to Dean's shoulder with a groan. "You have no idea. N-never been affected like that before," he panted, his hips snapping against Dean's thighs now, "never--never until you." He came inside Dean with a shout, gripping Dean's hips so hard they were already bruising.

They laid there for a while breathing together and smiling at each other.

"It really turns you on doesn't it?" Dean asked, raking his fingers through the other mans hair.

"Yes," Castiel mumbled into the pillow. He turned his head to Dean and smiled. "Does that make me a bad person?"

"The worst," Dean said playfully, leaning over to kiss him as his stomach decided to growl.

Castiel sighed. "I should've fed you before---," he gestured between them with a smile, "I apologize."

Dean stretched with a loud groan, looking over to the nightstand. "It's four thirty in the morning, Cas. Little late for meatloaf."

"Pancakes it is. Be back in a bit," Castiel grinned, kissing Dean on the cheek before swinging his legs over the bed and standing. Dean propped himself up on an elbow and watched as Cas walked naked into the bathroom. He heard the shower turn on as his eyes drifted close, exhaustion finally taking hold.

_"...went very well. You should have seen it," _Castiel chuckled,_ "I told you....no, I don't think so and if a problem arises I'll handle it. We should discuss The Roman problem soon, who knows what Alfie told them."_

The floorboards creaked as Dean stepped into the kitchen, making Castiel turn. He smiled and pointed to the counter where a stack of pancakes were sitting.

"Call when you have a meeting set up?...yes, ok. Goodbye, Michelle."

Castiel sat his phone on the counter and walked over to Dean, kissing him on the cheek. "Michelle is very impressed with you."

"Apparently she isn't the only one," Dean mumbled as he sat on the bar stool. He winched and wrinkled his forehead. "I think you broke me."

Castiel licked his lips and rubbed Dean's shoulders, leaning down close to his ear. "I apologize. It's just fascinating taking you apart and putting you together again."

Dean groaned as a shiver shot through his body. "C'mon, man," he muttered, "tryin' to eat here."

Castiel kissed the mans ear with a chuckle. "If you must." He rounded the corner and poured them both a cup of coffee, sliding one across to Dean. "The Romans will need to be dealt with soon," Castiel sighed into his cup.

"Dealt with as in," Dean stuck his pointer finger to his temple and lowered his thumb. He stuffed a forkful of pancake in his mouth and chewed loudly.

Castiel rolled his eyes. "Eager aren't we? Hopefully we can set up a meeting with the families and talk. Otherwise, yes," he mimicked Dean's finger gun with a smirk.

"Who's eager now?" Dean winked.

Castiel lowered his gaze and drummed his fingers on the counter top. "What Alfie did was unacceptable. He didn't just betray Michelle, he betrayed all of us, including you." He braced himself against the counter. "The Romans probably know by now that Alfie has been...retired. They'll have come up with a contingency plan for getting intel. We need to find a way to keep the families separate but at peace with each other." He ran a hand down his face and sighed. "Fucking Alfie. Do you know how long it's been since there was a war between the families?" He looked at Dean who shrugged.

"I've been doin' this for what, a week? Cas, I got no idea what to do here. I'm just along for the ride. Where you go, I go." Dean sipped his coffee and watched Castiel's face drop. "What," Dean cocked his head. "What'd I say?"

Castiel shook his head. "You're right. Jesus fuck, you're right. I'm so sorry Dean." He raked his fingers roughly through his hair. "I never---Dean is this what you _want _to be doing? Helping me torture and kill people? Jesus," he ran a hand down his face roughly and hung his head.

Dean puckered his lips and shrugged again. "Listen, Cas. I told ya, I'm in it with you now. I got a crash course with Alfie and I know I still have a lot to learn, but I'm not goin' anywhere unless you make me." He lifted a forkful of pancake to his mouth and smiled around it.

Castiel bit his lip and shook his head. "I don't know what I did to deserve you. You're so loyal so quickly."

"That reminds me," Dean mumbled around a mouthful of food. He pulled out his wallet and took out a folded piece of paper.

"Dean---"

"Shaddap, Cas," Dean waved a hand at the man before sliding the check across the counter. "I don't---I don't need this. Hell I don't think I was ever really in it for the money. Yeah it was a plus at first, but if you're alright with this just bein' us and not about this," he tapped the check with his pointer finger, "I'm in."

Castiel smiled and picked up the check. He pulled a lighter and his cigarettes out of his pocket and flicked it the lighter, setting the piece of paper on fire. He plucked a cigarette out of it's pack and held it to his lips, lighting it off the checks' flame. He took a long drag and winked at Dean.

Dean rolled his eyes and reached out, beckoning Castiel with two curved fingers. Castiel handed Dean the cigarette as his phone chimed. He looked at the screen and sighed.

"What?" Dean asked, blowing smoke out his nose.

"Meeting with the Romans. Today. Get dressed."

Obnoxiously large houses must be a _thing_ for people in the mafia. Dean rolled his eyes as they pulled up the driveway, taking in the artfully trimmed hedges and trees.

"You'd think you guys would live in normal looking houses. Nothin' says 'I've got too much money' like three story mansions and marble statues."

Castiel fidgeted nervously in his seat, adjusting his tie for the sixth time. "What?" he asked, somewhat annoyed.

Dean reached over and grasped Cas' hands gently. "It's gonna be fine, Cas," he whispered. "You're a badass and whatever happens in there---we'll deal with it, alright?"

Castiel looked down to Deans hands, kissing his knuckles. "You're right--I know. I'm just--," he sighed heavily, nuzzling into Dean's palm. "When we get in there, please, just let me do the talking. They don't know you and you're barely vetted. The families have all known each other for decades and you're so new. Plus with your dad---" Castiel pinched his eyes shut and sighed heavily.

"Cas," Dean squeezed the mans hands tight, lowering his head to catch Castiel's eye line. "It'll be fine. I'll keep quiet, scouts honor." He held two fingers in the air and grinned.

"Like you were a scout," Castiel snorted.

A very stiff looking maid lead them down a hallway towards the back of the house. Like Castiel's, it was lined with portraits of creepy old men, but Dean didn't recognize any of them from Cas or Michelle's house. The angry maid opened the door and ushered them inside, half slamming the door behind them.

Michelle and a few men Dean didn't know were already seated at a long table opposite each other.

"You must be Castiel," the man said, standing from his chair. He was tall and skinnier than Dean with a pointed nose that begged to be punched. "Come, sit."

Castiel walked ahead slowly, reaching out and taking the man's offered hand. "Dick, always a pleasure," he mumbled, "This is my associate---"

"Your soldiers have their _own _associates, Michelle?" he interrupted, turning his head over to scoff at Michelle. The other men at the table snickered as they watched Dean stuff his hands into his pockets.

"What can I say," Michelle smiled, ashing her cigarette. "Things are going well for us. Bringing on new people--the best of the best. Dick," she waved a hand towards the men, "meet Dean Winchester."

Dick's smile faded into a sour frown as he turned to face Dean who was staring at him intently, fists balled in his pockets.

"Well now," he breathed out, "never thought I'd see one of you again. I knew your daddy. Fine piece of work, that man," Dick smiled wide.

"So I've heard," Dean bristled. "Apple doesn't fall far from the tree. Just ask Alfie. Oh,--wait," Dean smirked.

Dick licked his lips as his eyes widened. "Yes, I hear you're quite the artist with an ice pick." He held out his hand towards the table. "Have a seat, we'll get this meeting officially started. I'm sure we all have other places we'd like to be."

Castiel's eyes narrowed, watching the other men size him up as they took their seats.

"Shall I begin, or weren't we finished measuring each others dicks yet?" Michelle glanced at Dean.

Dick let out an annoying laugh and slapped his hands on the table. "Oh, Michelle, how I've missed your wit. Please, proceed."

"We received word a week ago that one of our men was secretly meeting with two of yours," she eyed the men across from her. "After further investigation we realized one of our own, Alfie, was conspiring with your men, trading intel for his own profit. We don't take these things lightly." She glanced at Dean. "I suppose we'd all like to know, after decades of peace between the families, why you would give your men such an order."

Dick raised his hands in the air and cocked his head. "Michelle, you know as well as I do that an uprising is the last thing we need. I have left your family alone as you have mine. I never ordered my men to do anything of the sort."

"So your men are acting on their own behalf?" Castiel scoffed. "I highly doubt it, unless you employ _much_ less intelligent workers than expected."

"I suggest you ask them yourself, Castiel," Dick motioned towards the men next to him.

Castiel cocked an eyebrow at one of the men. "Well?" he asked.

The man sitting back in his chair with his arms crossed huffed a laugh through his nose while the other one leaned forward, lacing his long fingers together.

"Answer the man," Dick ordered.

Lounging man rolled his eyes. "Never heard of this 'Alfie' guy before." He shrugged his shoulders and looked over to Dick. "Can I go now, dad? These meetings are boring as fuck and I have other shit to do today."

Dick leveled a look at the man and smashed his fist on the table. "Answer me honestly, Adam or so help me---"

Adam jumped in his seat. "Dad, I---"

"Aw come on, Dick," the other man said, still staring at Dean, "little Adam here wouldn't do anything like that would you?" He turned to the boy and smirked. "I know he's your son but he isn't exactly in the life, is he?" He patted Adams shoulder roughly, his long fingers digging in. "He'd rather be out chasin' tail than coming up with ways to destroy the family."

Adam pulled away slightly, grimacing at the mans touch.

"Alistair, anything to add?" Michelle sighed, blowing smoke in his direction.

"Michelle," he purred, "if you think I'd have anything to do with this you're mistaken." He turned his gaze to Dean. "Why are you here?"

Dean bristled and glanced at Castiel. "I was invited. Why are _you _here?"

Castiel gripped Dean's leg under the table tightly. "Alistair is Dick's right hand man, Dean. He oversees all of their...transactions."

Dean ran a hand down his chin and hummed. "So then we should be grillin' you, not the kid."

Alistair let out a nasally laugh and crossed his arms over his chest. "I'm an open book, Dean."

"Alfie said there was a new Capo in town, I'm assumin' that's you," Dean pointed to Dick but didn't take his eyes off Alistair.

Dick raised his hands and chuckled. "Absolutely not. I'd never go up against Michelle. We've lived peacefully for quite some time."

Castiel's eyebrows shot up and looked to Michelle. They shared a knowing nod as she ashed her cigarette. "I think that's all we need, Dick. We'll be in touch."

Michelle stood, followed by Castiel and a very confused Dean.

"It was wonderful to see you again," Dick said, raising to shake Michelle's hand. "And Dean," he reached out his hand towards him, "nice to see you're keeping up the Winchester name."

Dean stared at his hand before turning on his heel and following Castiel out the door.

Michelle pushed the large doors open and sighed into the night air. She shook her head as she held up her lighter, sparking Castiel's cigarette to life. "Just as we thought," she sighed.

Castiel nodded and took a long drag before handing it to Dean. He took it as he watched Cas' face contort.

"Anyone gonna fill me in? I can't read minds like you two apparently can." He took a drag and flicked the ash.

"Alistair is getting every ounce of info he can on us. Then he's going to overthrow Dick. _He's_ the new Capo Alfie was talking about.

Dean swallowed thickly. "How bad's it gonna get?"

Michelle walked to her car and flung open the door, clenching her jaw.

"Bad."


	10. Chapter 10

**Summary for the Chapter:**

> I'M BACK, BITCHES!  
Have a short chapter while I write the next one
> 
> **WARNING**  
Smut, knife play, come play and a teeny bit of blood play in this chapter. It's not horrible or gross I promise. This is what happens when I get carried away.  
Ooohhh wellll

Castiel led Dean through his house quickly. He tugged on his hand every few steps, making him pick up the pace.

"Cas where the fuck are we doing?" Dean tried to pull out of Castiel's grasp but it only made him hold on tighter.

"When is the last time you talked to Sam?" Castiel asked without looking back. He pushed open a door that lead down a dark flight of stairs. He reached up and pulled a long string, lighting up the lower half of the room.

"What? Why? What's Sam got to do with---ugnh!" Dean's eyes widened as Castiel spun around and shoved Dean against the wall of the staircase. He was much taller than Castiel like this, being two steps above him, but it Cas still had the upper hand. "Answer me," he growled.

Dean's Adam's apple bounced nervously in his throat as he looked into Castiel's wild eyes. "'Bout a week," he answered quietly. He placed his hand on the other mans arm gently. "What's goin' on, Cas?"

Castiel sighed heavily, loosening his grip. "Call Sam, make sure he has no plans of coming home anytime soon. Make it seem like a casual call." He looked into Deans eyes for a moment before kissing him softly. "Thing are going to get very bad very quickly and I don't want him to accidentally getting caught in the middle of this." He took Dean's hand and led him down the stairs.

Dean gasped as Castiel walked up to the far wall, lights illuminating the shelves of guns and knives. Castiel plucked a few smaller ones from their hook and set them on a table nearby.

"When's the last time you shot one?" he asked, inspecting a magazine before sliding it into the well of the gun.

Dean swallowed hard, eyeing a sawed-off shotgun that reminded him of his dad. "Not---not for a long time. Maybe...ten years?"

Castiel turned and raised an eyebrow, a smirk pulling at his lips. "We'll need to fix that then, won't we?" he asked, handing him a pistol.

Thirty minutes and about a hundred rounds later, Castiel deemed Dean fit to wield a firearm.

"I told you I didn't need practice," Dean smirked, holding up his target. The figures head was shredded and had various holes where Castiel instructed him to aim.

"Don't get cocky boy," Castiel chided, lifting Deans chin with a finger. "It'll be much different when you're shooting at a person. Targets are easy, they don't scream or bleed," he chuckled, lightly tapping the side of Dean's face.

"Not cocky. Confident," Dean said darkly, wrapping his fingers around Cas' tie. "I can do this, Cas. I'm not afraid."

Castiel's eyes darkened as he stepped up to Dean, their noses bumping. "And when you shoot someone? When they start bleeding out, begging you to spare their life, what then?"

"Can't beg for mercy with a bullet in your head," he whispered, his lips moving against the other mans.

In a flash Castiel's fingers were buried in Dean's hair as his tongue invaded his mouth. Dean fisted Cas' tie, yanking him forward as he backed himself up against a table. Their clothes fell to the ground, piece by piece between frantic kisses until Dean was bare and bent over the table. Castiel pressed his cock against Dean's ass and rutted against him.

"You never cease to amaze me Dean," he growled.

Dean panted against the table, his hands pressed firmly on either side of his head. He felt something cool and hard run up his back making him shiver.

"And if you run out of bullets?" Castiel asked darkly.

Dean craned his neck over his shoulder, immediately moaning as Castiel raised a small blade to his throat. He chuckled and licked his lips. "I don't know if you know this or not," Dean grunted as his left hand flew up and gripped Castiel's wrist. He threw his head back, almost catching Castiel in the nose. He stood quickly and gripped both of Castiel's wrists in one hand, spinning him so he was pressed against the table. He plucked the knife out of Cas' hand and held it to his cheek. "But I'm _much_ better with a knife than a gun." Castiel's eyes widened as he felt the blade nick the skin on his cheek. Dean leaned in close, his breath beating off the other mans face. "After all, it's in my blood." A wide grin spread across his face before he leaned in and licked the spot where he sliced into Castiel.

He felt Castiel tremble underneath him which elicited a brand new sensation to course through his veins. He raised an eyebrow and leaned in, licking Castiel's bottom lip. Castiel groaned and opened his mouth, licking into Dean's as he cupped the mans cock. 

"The things you do it me," Castiel growled, pumping Dean roughly. "You have no idea."

Dean slapped the knife down on the table before digging his fingers into Castiel's back. His forehead pressed against the other mans chest as he fucked into Cas' hand, biting and licking any skin he could reach. Castiel ran his thumb over the wet slit of Deans cock before pumping hard, pushing Dean over the edge. He came with a shout, nails drawing blood on Castiel's back as he rode out his orgasm.

Castiel released Dean's cock and spun him around, pressing him face down on the table. He spread Dean's cheeks and slicked his hole with his own come, fingers roughly massaging around the muscle. He gave no warning before shoving the tip of his cock inside, making Dean gasp. He ran his hand down Dean's back, nails leaving red streaks behind. He grinned to himself as he watched his cock press fully inside before setting a quick pace.

"Never---never get tired of this," he hissed through clenched teeth. "Watching every ounce of innocence slip away," he thrusted harder. Castiel gripped Dean's hips and pounded into him, reveling in the sounds Dean was making. "I love it. _I love it,_" he groaned loudly as he came inside Dean, pumping him full. He pulled out, much to Dean's dismay, and tapped on his hips, signalling him to stand.

Dean turned around and faced Castiel with a grin creeping across his face. Castiel ran his hand over the other mans face and down his jawline. "Fucking perfect," Castiel sighed.

"Seriously, Dean, what's going on?"

Dean rolled his eyes as he looked out the window and down at the statue in the courtyard.

"Nothin' Sammy! Can't I just call and see how my brother's doin'?" He heard Sam sigh and a keyboard clacking on the other end.

"Ok then. Uhm, everything's good here I guess. Just studying for finals. How's work?"

Dean froze. "Uh--yeah. It's---it's good. Pickin' up extra shifts at the bar. Gabriel is still an ass, don't think that's ever gonna change. But uh, yeah. All's good there."

"Yeah? Is that why there's like three thousand more dollars in my bank account then usual?" Sam chuckled.

Dean turned to Cas with wide eyes. Castiel looked up from his desk and ashed his cigarette. He shrugged innocently before returning his attention to the pile of papers on his desk.

"Uh, yeah. Told ya, it's been good here." Dean scowled walking over to the desk. "So when you think you'll be coming home?" He plucked the cigarette out of Cas' fingers with a scowl and took a long drag.

Sam sighed on the other end. "Ah, not til after finals. Maybe a month or so?"

Castiel nodded while reading his papers, silently taking note. 

"Yeah ok, good. That's good. Can't wait to see you man." He frowned slightly. He hadn't realized how much he actually missed his brother until he heard his voice. "But uh, I'll let you go---study or whatever. Good luck on your finals."

"Thanks. Talk to you later jerk," Sam huffed.

"See ya, bitch." Dean pressed end and tossed his phone on the desk. He took another drag before handing the cigarette to Castiel. "We're good," Dean sighed as he sat in the chair in front of Cas' desk. He eyed the man suspiciously. "Three grand, huh?"

Castiel ran his tongue over his bottom lip and smiled.

"I thought we weren't doin' that anymore?" Dean crossed his arms and sat back in the chair.

Castiel looked up and reached his hand out. Dean sighed and reluctantly leaned forward and took it. "You're part of the family now, which means Sam is too."

Deans jaw clenched as he tried to pull away, but Castiel kept his hand in a tight grip.

"Not like that. He doesn't ever have to know about all this. Although," he rubbed his chin with his free hand, "it would be nice to have a lawyer in our pocket." He chuckled when Dean scowled at him. "Kidding," he reassured. "But he _will _be taken care of, financially, until he can support himself. I won't hear another word about it. Understood?"

Dean relaxed and ran his thumb over the other mans knuckles. "Fine," he snapped. "But tone it down man, I made like five hundred bucks on a good week. He's gonna know somethin's up if you keep sending him that much."

Castiel narrowed his eyes and smiled. "Fine. A thousand a week it is." He held up a hand as Dean opened his mouth to argue. "You _did_ just say you were picking up extra shifts." He smiled wide as Dean tossed his hand away and slunk deep into his chair.


	11. Chapter 11

**Summary for the Chapter:**

> Dean meets with Dick.  
Michelle comes for dinner.

Dean exhaled smoke through his nose as he tapped the burning end against the crystal ashtray. Castiel fumbled with his tie, glancing at Deans reflection in the mirror.

"To think, you weren't really a smoker until you met me." He turned and flashed a wicked grin to Dean who was still laying in bed, surrounded by a red blanket.

Dean huffed a laugh as he snuffed out his cigarette and stood, letting the blanket fall to his feet. He walked up behind Castiel and let his hands glide up the mans torso until his fingertips brushed against Cas' tie. Hooking his chin over Cas' shoulder, he straightened it and patted his chest before kissing the side of his neck. "You did say you were looking forward to--what was it?-- 'eradicating my innocence'?" Dean let his hand fall to Cas' belt as he nipped the skin on the back of Cas' neck.

Castiel turned and cocked an eyebrow as he let his fingers trace Dean's jawline. "And how are you feeling about that?"

Dean lowered his head and fidgeted with Cas' belt. "What do you mean?"

Sighing, Castiel pulled Dean's chin up with two fingers. "I think you know what I mean."

"I dunno," Dean shrugged. "I mean, it's still a lot to take in. It's hard to replace the feelings I had for my dad with new information." He let his hand fall from Cas' hip as he walked over and sat on the edge of the bed. "I guess I'm just glad it was me and not Sam. He's not---he isn't cut out for this." He ran a hand down his face and let it slap against his thigh. A pained look washed over his face as he cocked his head. "Is it," Dean sighed hard and hung his head. "Cas, it feels right. Like this is what I'm supposed to be doing. Is that bad?" He looked up at Castiel who was trying to keep a straight face but failed. He grinned as he walked forward and knelt in front of Dean. He picked up Deans hands and kissed his knuckles before nuzzling into his palm.

"Dean," he sighed, "some people were born to be doctors. Some were born to be musicians. You," he squeezed Dean's hands and looked into his eyes, "you were born to this. The Winchester name strikes fear in the hearts of our enemies. _You_ strike fear in them. You don't know Alistair very well yet, but he's never scared. _You _scare him." Dean rolled his eyes and shook his head before Castiel's hand whipped up and gripped his chin tightly. "I mean it," he said sternly. "Dean, things are going to get very, very bad between the families and I need you to be ready. We'll need all the help we can get."

Dean swallowed hard and furrowed his brow. "Shouldn't we tell Dick about Alistair? I mean, the guy is an asshole but he deserves to know what his second in command is planning."

Castiel stood and crossed the room, picking his jacket off the back of a chair. "Michelle has already advised him not to trust Alistair but he won't hear of it. He's been with Dick for many years and doesn't believe he'd do anything to hurt the family," he sighed as he buttoned his suit coat.

"He's not going to see it coming. Shit," Dean hissed as he stood and opened his closet.

Castiel whipped around. "What are you doing?"

"I'm gonna go talk to him," Dean grumbled as he pulled on a pair of jeans.

"No. Absolutely not." Castiel's hand gripped Dean's wrist hard. "I will not have you walk into a proverbial lions den alone."

"Cas," Dean pulled his wrist free before buttoning his flannel, "you said it yourself. I'm in this. If I can talk to him and make him see what a slime ball Alistair is without all the ass kissing that went on in that meeting, then I'm going to do it."

Castiel cocked an eyebrow and crossed his arms. "Ass kissing?"

Dean looked up at Castiel as he was lacing up his boots. "You guys beat around the bush so bad it makes my head hurt." He stood with a sigh and took Cas' hands and pulled him close. "I'm just going to go over, have an actual conversation with the guy. If he doesn't like what I have to say, then at least I can say I tried." He kissed Cas' forehead and turned to leave.

"Dean," Castiel tugged him back by his hand. He closed his eyes and sighed. "Please be careful." He turned his wrist over and glanced at his watch. "I have a _meeting _in twenty minutes that I can't be late for, so if you're insisting on going without me, I'm trusting you not to get shot. Or stab anyone."

"Aww, look at you all worried for little ol' me," Dean cooed before kissing Castiel on the lips. His hand threaded through the other mans hair before he pulled away and smiled. "I promise. Cross my heart."

They walked to the front door and kissed goodbye in front of the marble statue.

"Have a good _meeting_ honey," Dean whispered, patting Castiel playfully on his ass.

Rolling his eyes, Castiel climbed into his car with a smile on his face. Dean waited for his car to pull up and got in, hearing the gates screech closed behind him.

Dean drummed his fingers on the arm of the chair. Dicks' receptionist let him into the office about twenty minutes ago, claiming he was already in a meeting. Muffled voices and forced laughter drifted from one of the rooms in the hallway as Dean pulled a cigarette out of his shirt pocket. He flicked his lighter just as the doors of the office swung open.

"I'd appreciate it if you didn't smoke in here," Dick said, coming around to sit in his chair. "Michelle has some leeway here but I assure you, Dean Winchester, you do not."

Biting the filter of the cigarette, Dean stuffed the lighter in his pocket. He plucked the cigarette from his teeth and slid it over top his ear.

"Sorry 'bout that," he grumbled. 

Dick smirked and laced his fingers together, resting them in front of him on the desk. "So, Dean, what brings you all the way across town? And alone, no less?"

Dean rested his elbows on his knees and sighed. "We don't know each other and I'm new to the business but I needed to talk to you about one of your men."

"Alistair," Dick guessed.

Dean nodded. "I understand you're close and he's been your number two for a long time, but Dick, you have to see what he's doing man. The meeting with Michelle and Cas was a total waste of time. Maybe they have too much respect for you to say what really needs to be said."

"And you don't?" Dick asked, cocking an eyebrow.

"Respect is earned," Dean simply stated. "Alistair is going to overthrow you and your whole operation. He started with Alfie, getting mass amounts of weapons from a kid who was too scared to stand up for himself and the family. Now we're down resources and money. I'm having a hard time believing you'd be ok with something like that. Alistair on the other hand--" Dean trailed off, shrugging.

Dick sat back in his chair, tapping his chin with a long finger. "I like you, Dean. You've got guts. And as you've said, you're new to this. You don't know the relationships we've built over the years and the trust that goes along with them. Al is one of my finest. He's never done anything without my permission and I'm having a hard time believing that he would go against me." He leaned forward and braced his elbows on his desk. "I'm inclined to think that little Alfie wanted out and was just skimming money to start a life of his own."

Dean shook his head. "No, I really don't think--"

"You don't _GET TO THINK," _Dick shouted, staring directly into Dean's eyes. "You think since you're Castiel's new lap dog that you can come into MY HOME and tell me how to run MY BUSINESS? I don't fucking think so!" Dick stood stiffly and nodded towards the doors. "Unless you have definitive proof that one of my own is deceiving me, get out." He punctuated the last words before sitting down and grabbing a stack of papers.

Dean stood and walked towards the door. He opened it roughly, his knuckles gripping the handle tightly.

"I hope the next time we see each other you don't have a bullet in your brain. Think about what I said," he turned his head over his shoulder, "and watch your back, Dick."

"Maybe we should put someone on him. It couldn't hurt to have extra eyes on the situation." Dean picked up a brown, stiff bristled brush and pulled Castiel by the shoulder, turning him around. Water from the shower beat off his back as he scrubbed Cas' fingernails. "You really should start using gloves," he scolded.

Castiel rolled his eyes as he watched Dean scrub dried blood from his cuticles. "I hate the way they feel on my skin," he said, wrinkling his nose. "And as for Dick," he sighed, "he's going to do what he wants to do. We can't change that. Tailing him would just be an insult to him." He watched as red water pooled around his toes.

"I'd rather him be insulted than dead," Dean mumbled.

Castiel took the brush from Dean's hand and set in on the showers shelf. "Why does this bother you so much, Dean?" He cupped Dean's face gently and kissed his forehead.

Dean shrugged and reached out, trailing a finger down Cas' chest. "It just seems unnecessary. He shouldn't die and have some asshole take over the empire he's made. Don't get me wrong," Dean grinned as he looked up at Castiel, "the guy lives up to his name, but he doesn't deserve to be taken out by one of his own."

Castiel sighed, rubbing Dean's shoulders lightly. "Let's not think about it anymore tonight. Michelle is coming over for dinner and drinks in a few hours and there's something very important I need to do before she gets here."

"Yeah, what's that?"

Castiel leaned in and nipped at Dean's ear. "I need to fuck you in this shower."

"I'm surprised Castiel let you out of his sight, let alone going to the Romans' alone." Michelle swirled her glass and glanced at Castiel out of the corner of her eye. "Tell me, Dean, who gave you permission to set up a meeting with Dick?"

Dean swallowed hard as his eyes bounced back and forth between the two. "Nobody did. I decided on my own." He speared a potato with his fork and chewed it quickly. He swallowed hard and set his utensil down, pushing his plate away. "I just wanted to talk to him. You guys don't seem to say what you really want to in those meetings," he shrugged and picked up his glass. "I thought I'd give him my two cents. That's all." He took a long drink of his whiskey and shakily set the glass on the table, feeling Michelle's eyes glaring at him.

Castiel bit the side of his cheek when Michelle rolled her eyes. He pulled a cigarette out and lit it.

"Michelle," he exhaled smoke through his nose, "no harm was done. If anything, Dean reinforced the idea that Alistair was going to betray Dick." He sighed and rolled the burning end of his cigarette in the ashtray. "And _must _we discuss business tonight? I'd like to have a day, or just a dinner, where we don't have to talk about plans or meetings."

The room was silent for a moment until Dean turned to Michelle.

"So, Alistair," Dean said, propping his elbows on the table.

"Good grief," Castiel sighed.

"What about him," Michelle asked with a grin as she rested her chin in her hand.

"Why do I even try," Castiel sighed, bringing his cigarette to his lips.

"How do we, you know---" Dean slid his finger across his throat and clicked his tongue.

Michelle laughed and sat back in her chair, crossing her arms. "Well that's a good question. Luckily, I'm in the room with two assassins." She looked at Castiel with a raised eyebrow. "I'm sure we can figure something out."

"Do you honestly think taking Alistair out is the answer? I'm sure he has others working for him, they'll just pick up where he left off after he's taken care of." Castiel frowned as Dean plucked the cigarette from his fingers..

"Then we take them out too," Dean smiled cheekily at Castiel before taking a drag.

"You can't possibly be thinking of taking out Dick's whole team," Cas chided.

"Not _all_ of them," Michelle said, waving a hand in the air. "Just Alistair and his closest confidants. Adam may need to be dealt with."

"You can't be serious. Dicks' son? No," Castiel shook his head and shoved his chair back as he stood. "Alistair? Fine. Killing Adam would start a war we aren't ready to fight." He turned to Michelle as he filled his glass with whiskey. "You saw him at the meeting. He's a child, he doesn't know anything."

Michelle turned to Dean. "I think you're making him soft," she whispered with a scowl.

"I make him a lot of things, soft isn't one of them," Dean said with a wink.

Castiel slumped against the rolling bar and sighed. "Adam will not be harmed. I won't hear anymore about it."

"Castiel, I think you're forgetting who's in charge here," Michelle said as she stood. "I'm open to negotiating but I will not be _told_ what to do."

Dean's throat clicked as he swallowed. Michelle really knew how to own the room and scare the shit out of everyone that was in it.

"M-maybe we can circle back to Adam after we find out who's all working with Alistair?" Dean offered. "As fun as it would be go to in guns blazing, we need to get intel on who's doing what and with who. Cas is right, Adam _may_ not need to be," he waved a hand in the air, "you know. But if he does," Dean looked at Cas with a frown, "I'll deal with it."

"Wonderful," Michelle said clapping her hands together. "I've taken up enough of your time tonight, gentlemen. Walk me out."

Michelle kissed their cheeks and said goodnight before walking to her car. Castiel leaned against one of the large pillars and watched as she climbed into her car.

"Sorry we talked your ear off tonight," Dean said as he wrapped his arms around Cas' waist. "It's just kinda cool getting to know---"

A massive explosion erupted in front of them. Michelle's car burst into flames as soon as she shut her door.

Castiel's arm shot out, shoving Dean behind him protectively. The sound made Dean cover his ears as glass sprayed over the driveway and porch.

Dean vaguely remembers Castiel frantically pulling out his phone and calling someone as he laid on the porch, watching Michelle's body burn to ashes in front of him. He climbed to his hands and knees, tears springing from his eyes as he watched the fire shoot into the night sky.

Movement in the hedges caught the corner of his eye. He gripped Castiel by his pants and pulled himself upright, looking off into the patch of woods across the lawn. In the treeline stood a tall figure, the flames from Michelle's car flickering off his face.

Dean reached up, gripping and turning Castiel's frozen figure towards his line of sight.

"Cas," Dean whispered.

"I see him," Castiel growled.


	12. Chapter 12

***Authors note***  
Hi *waves* remember me? I know, it's been like....way too fucking long right? I haven't forgotten about this story.  
In fact, I'm writing again and plan on finishing this week! I'm so sorry I've been away but, y'know, life happens.  
There will be at least one more (knowing me there will be 2) chapter in this story. I need to give the boys an ending they deserve.  
I love all of you!! Thanks for waiting and being patient while I got my shit together


	13. Chapter 13

The funeral was a quiet affair. At least the Romans' were kind enough to let the family grieve in peace.

Dean watched as Castiel and the other soldiers carried Michelle's silver casket through the pouring rain, gripping his black umbrella hard enough to turn his knuckles white. His eyes constantly darted around the small group of people and the treeline to the south, praying Alistair was dumb enough to show his face here. The gun tucked under his suit jacket felt like it weighed a ton and made his trigger finger itch.

He let his knuckles brush against Castiel's while the priest said his kind words, offering the slightest bit of comfort without making either of them look weak in case prying eyes were watching. Dean swallowed hard as he placed a single white rose on his friends coffin.

"We'll get him, Michelle. I fucking swear it."

Castiel pulled his tie off and tossed it on the bed. Dean watched as he silently removed his shoes and suit jacket, feeling small and awkward standing in the doorway.

"Hey, uh, I'm gonna run home for a bit." He scratched the back of his neck and sighed. "I think you might need some time alone an---"

"Do what you need to," Castiel said quietly as he tossed his watch on the nightstand.

Dean frowned and walked up behind Castiel, wrapping his arms around him. "M'comin' back, you know. I'll be alright," Dean muttered between the other man's shoulder blades. He felt Castiel take a deep breath and let it out slowly.

"I'm not worried about your wellbeing. I know you can take care of yourself."

"Then what're you worried about?" Dean asked, running his hands up and down Cas' arms.

"The future," Castiel confessed. He turned in Dean's arms and rested his hands on either side of his neck. "The families," he shook his head. "I never thought something like this would happen. And now that it has, I don't know what to do." He looked at Dean, his eyes red rimmed and tired and shrugged.

"We'll figure it out. Hey," Dean pulled Castiel's chin back up when he hung his head. He kissed Cas' frown and offered him a small smile. "I promise. You 'n me, alright?" Castiel nodded weakly. "I'm gonna go pack up a few things at my place. Why don't you take a shower while I'm gone and I'll be back in a bit." Dean cupped Castiel's face and kissed him softly before walking out of the room.

Walking into his own apartment felt....strange. It had been a while since he'd been home, thankfully he didn't have pets or plants that needed attention. He walked into his bedroom and began stripping out of his suit. He took the gun that was strapped to his back and tossed it on the bed before rifling through his dresser. Dressing quickly in a t-shirt and jeans, he dug in his closet and pulled out a green duffle bag and began stuffing it with clothes and a few precious photos of his family. He ran his finger across the faded picture of his mom, the only one he had now, and smiled. He wondered briefly if she knew about John before shaking his head.

"She really was a pretty little thing, wasn't she?" a voice called from the doorway.

Dean spun on his heel and reached for his gun, remembering too late that it was on the bed under his suit. "The fuck you think you're doing in my house, Alistair?" Dean hissed.

Alistair squinted at the door jamb and scratched at a the peeling paint. "I wouldn't exactly call this dump a house. Plus, you haven't been here since Cassie sunk his hooks into you. What's it been, Dean? Two weeks?"

Dean clenched his jaw. He knew someone had been watching them from the start. "Gotta tell ya man, you need better tails," Dean said with a light huff. "First thing I saw at the tailors was your van. Cliche much?" Dean bent down to pick up his bag and heard the telltale click of a hammer being pulled back.

"Wouldn't do that if I were you Dean," Alistair sneered as he pointed his gun at Dean's head. He glanced at the suit on the bed. "How was the funeral anyway? I couldn't make it."

Dean snarled and took a step forward. "Michelle had nothin' to---" The words caught in his throat as Alistair stepped forward and pressed the barrel against his forehead.

"That _bitch_ was keeping me from rising in the ranks. Dick wouldn't dare look in her direction, let alone go above her head. But now," Alistair hissed as he stepped up nose to nose with Dean, gun shaking in his hand, "he doesn't have a say. That pathetic excuse of a man is in little, itty-bitty pieces and tossed over the side of a ship by now. His little bitch of a son is next."

Dean bristled and heard his own words ricochetting around in his skull. _Watch your back, Dick._ He swallowed hard and eyed the thin man in front of him. "Adam's got nothin' to do with this. He's just a kid. Dick didn't raise him in the life, he doesn't know---"

"Dick? Oh, no-no-no, Dean." Alistair lowered his weapon slowly, dragging it down Dean's jaw and shoving it up in the soft spot under his jaw. "Adam came into Dick's possession when he was just a little thing. Couldn't have been more than a year old." His smile was sharp and foul, his tongue dancing behind his teeth. "You're daddy sure did get around back then," he growled.

Dean's fist collided with the side of Alistair's ribs before he gripped the gun and dislodged it from the man's fingers. He stared down at the man who was gasping for air on the floor. "Liar," Dean shouted. "You're a fucking liar!"

Alistair raised a hand in surrender as a feral grin spread across his face. "Surprised Cassie didn't tell you already. He knew the whole time."

"No," Dean spat. "He wouldn't---" Dean lifted the gun to Alistair's head.

"Your poor mamma," Alistair whispered, nodding his head towards the picture that had fallen on the ground. Dean's eyes flicked to the worn picture just as Alistair shifted on his knees. Dean saw a flash of silver and the sting of a blade in his gut before everything went black.

"....-ime to wake up, pretty boy. Oh Deeeean."

A sharp slap across his face made Dean's head snap up. He immediately groaned and tried to hold his stomach but his hands wouldn't move. He yanked at his restraints but quickly stopped when he felt something warm pool in his lap.

"Wouldn't move around too much if I were you, Dean. That's a pretty big slice you got there." Alistair stepped out of the shadows and into the light, slithering up to Dean like a snake. He crouched down in front of Dean and smiled.

"Cas---" Dean panted heavily. "Cas'll come for you."

Alistair tsked tapped his finger on Dean's knee. "Aw, Dean. Don't you get it yet?" He lifted a long, skinny finger and pressed it into Dean's wound, crooking his finger. Dean bit his tongue and held back a scream. He wasn't giving this piece of shit the satisfaction. "That's what I'm hoping for."

As if on cue, Dean's phone vibrated in his pocket. His watery eyes watched as Alistair dug in his pants and retrieved the phone. He answered and hit the speakerphone button.

"Sorry, Cas," he hissed, drawing out the S. "Dean can't come to the phone right now."

The line was silent for a few seconds before Castiel spoke. "Where is he?"

Alistair smiled and looked at the blood oozing from Dean's shirt. "Oh he's right here, but I gotta say, Cas, I'm not sure how much longer he's gonna be conscious."

"What do you want?" Castiel asked, his voice hard and cold.

"Your head on a stick, of course. More importantly, the business, Castiel."

Dean panted as his head hung forward. "Cas," he moaned. "The fucker. He----" The back of Alistair's knuckles collided with the side of Dean's face harshly.

"Like I said, he doesn't have a lot of time. Why don't you come save your boy toy and we can talk."

"Where are you?" Castiel growled.

"Warehouse seven. Your precious boy is sitting in the same spot where Alfie met his untimely end. Tick tock, Cassie."


End file.
